Roberto Ballini

University of Camerino | UNICAM · Dipartimento di Scienze Chimiche

Herein we report a new practical and efficient multistep syntheses of 1”‐ and 2”‐hydroxycannabidiol metabolites. Both products and intermediates were fully characterized, and the target metabolites were produced in good overall yields.

Due to its excellent properties, poly(ethylene terephthalate) (PET) is one of the most produced and consumed polymers. Among plastics, it represents the main contributor to environmental pollution. Following the circular economy model, the chemical upcycling of PET reduces the amount of waste generated and transforms it into high-value products. Th...

Herein, we report a new application of β-nitroenones as valuable building blocks for the preparation of polyfunctionalized homoallylic alcohols; they can be used as key precursors of conjugated nitrotriene systems. The synthesis of homoallylic alcohols was performed exploiting the chemoselective addition of metal allylating agents to the ketone moi...

Herein, we report a new and stereoselective conversion of β‐nitro‐β,γ‐unsaturated ketones into conjugated dienones, a versatile class of electron‐poor alkenes, widely exploited in organic synthesis as source of highly functionalized molecules. Products were isolated in good yields and the method tolerates a variety of functionalities.

The conjugate addition of nitroalkanes to electron-poor alkenes is a widely used process which only in the late nineties of the last century has efficiently evolved in its asymmetric version....

Herein, we report a new one‐pot synthesis of polysubstituted carbazoles starting from β‐nitro‐β,γ‐unsaturated‐ketones and indoles. The process is based on a Friedel‐Crafts reaction of indoles to nitroolefins supported by 2,2,2‐trifluoroethanol (TFE) followed by an acidic‐promoted and microwave‐assisted intramolecular cyclization, that involves the...

Herein we report a new practical and efficient preparation of the flavonoid Luteoloside. The title target has been obtained with an excellent overall yield of ~40% via a four multistep synthetic approach.

Cannabidiol is one of the main non‐psychoactive cannabinoids present in Cannabis sativa and in the last decade, it is gaining great interest among the scientific community for its pharmaceutical, nutraceutical and cosmetic applications. Herein, we report the first continuous flow chemical synthesis of cannabidiol (CBD) and its analogues cannabidiva...

We report herein an unprecedented conversion of β‐nitroenones into β‐nitro‐β,γ‐unsaturated ketones. The reaction proceeds under microwave irradiation, furnishing products in good yields and excellent diastereoselectivity. The mechanism of the reaction has been rationalized by means of DFT modelling, which showed that sequential enolization/isomeriz...

Highly functionalized furans are the key scaffolds of many pharmaceuticals and bioactive natural products. Herein, we disclose a new fruitful synthesis of polyfunctionalized furans starting from β-nitroenones and α-functionalized ketones. The protocol involves two steps promoted by solid supported species, and it provides the title targets from sat...

Aliphatic nitro compounds having an acidic hydrogen in the β‐position, with respect to the nitro group, are prone to undergo the elimination of nitrous acid, mainly under basic conditions, affording a C=C double bond. Until a few decades ago, the literature reported some examples of the application of this elimination as a strategic step in the syn...

We report herein a general and efficient continuous flow‐based protocol for synthesizing thiophene‐2‐carboxylates starting from ketal‐functionalized β‐nitroacrylates. The protocol involves (i) a promoter‐free conjugate addition of thioacetic acid to β‐nitroacrylates, (ii) a base‐induced elimination of nitrous acid, and (iii) a final acid‐promoted d...

A synthetic approach to a new class of allyl nitro derivatives is reported. (2-Acetoxy)allyl nitro compounds have been prepared for the first time in a four step procedure by a preliminary reaction of nitroalkanes with 2-(phenylselenyl)acetaldehyde. After the acetylation of the obtained nitro alcohols, the unsaturation is installed by an oxidation...

Nitroalkanes, mainly the primary ones, are the key starting materials for the synthesis of a large variety of important targets. However, in spite of their strategic synthetic importance, every single type of nitroalkane and every single procedure are relegated to individual contributions. Thus, this review represents the first exhaustive collectio...

A new efficient synthesis of racemic anatabine is reported. The title target was obtained in an excellent overall yield of 70%, by a five-step synthesis, using cheap reagents and mild reaction conditions.

Herein, we report a new efficient and sustainable synthetic protocol for the preparation of -nitro esters starting from cyclic 2-nitro ketones. The method involves the use of polymer bound BEMP...

A new simple and efficient synthesis of 6‐nitroindoles, starting from N ‐carboxylalkylpyrrole‐2‐carboxaldehydes and protected β‐nitro ketones, has been developed. The method involves two distinct domino processes, respectively performed under flow chemical conditions and microwave irradiation. 6‐Nitroindoles were produced in good to excellent overa...

Buy Article Permissions and Reprints Abstract A new, simple and efficient chemoselective reduction of β-nitro enones to provide substituted β-nitro ketones, a strategic class of compounds, under solid heterogeneous palladium catalysis and in the presence of triethylsilane is presented. Key words aliphatic nitro compounds - heterogeneous catalysis...

In order to assess if an extra virgin olive oil (EVOO) can be acknowledged with the health claim related to olive oil polyphenols (Reg. EU n.432/2012), a new method to quantify these species in EVOO, by means of liquid-liquid extraction followed by HPLC-DAD/MS/MS of the hydroalcoholic extract, has been developed and validated. Different extraction...

starting from pyrroles and β-nitroacrylates

The demands of modern society for new functional chemical entities have driven the development of novel methods that are revolutionizing the way we think, plan, and optimize chemical processes. Chemical industries, in general, use a large volume of organic solvents and catalysts in their manufacturing processes. However, the toxic and volatile natu...

Quinoline-2-carboxylates are an important subclass of quinoline derivatives largely present in a variety of biologically active molecules, as well as useful ligands in metal-catalyzed reactions. Herein, we present a new one-pot protocol for synthesizing this class of derivatives starting from β-nitroacrylates and 2-aminobenzaldehydes. In order to o...

This study sought to develop and validate a quantitative method to analyse short chain free fatty acids (SCFAs) in rat feces by solid-phase micro extraction and gas chromatography (SPME-GC) using the salt mixture ammonium sulfate and sodium dihydrogen phosphate as salting out agent. Conditioning and extraction time, linearity, limit of detection an...

Herein, we present a new general and efficient protocol to synthesize pyrrole-2-acetic acid derivatives starting from pyrroles and β-nitroacrylates, under fully heterogeneous conditions.

This review article reports new procedures and practical application of the nitro to carbonyl conversion that appeared in the literature after our comprehensive report published in 2004. Beside traditional and well explored reactant systems, new procedures including the utilization of molecular oxygen and photoredox catalysis have been introduced f...

Abstract The reactivity of silyl enol ethers with β-nitroenones was successfully exploited for synthesizing functionalized polycarbonyl frameworks, in very short reaction times and in good yields.

The nitroaldol (Henry) reaction of 2-oxoaldehydes with a variety of nitroalkanes, under basic heterogeneous conditions and microwave irradiation, affords 1,2-diketones in a one-pot way. The key step of the process involves the nitrous acid elimination from the nitroalkanol intermediates instead of the standard water elimination

Herein, we present a new, efficient, one-pot synthesis of pyrrole-2-carboxylate derivatives starting from ketal-functionalized β-nitroacrylates in combination with primary amines under acidic heterogeneous conditions.

1,3-Dinitro alkanes are an emerging class of nitro alkanes that act as bidentate nucleophilic species suited to undergo a variety of reactions with an array of electrophiles. The goal of this microreview is to demonstrate the synthetic potential of these nitro derivatives, reporting both (i) recent procedures for the convenient synthesis (symmetric...

Reaction of α-amido sulfones with nitro ketals promoted by KF on alumina provides the corresponding adducts which upon treatment with p-toluenesulfonic acid generates the corresponding N-alkoxycarbonyl-2,5-disubstituted pyrroles. The latter transformation involves a cascade process including ketal cleavage, ring closure and final aromatization by n...

Photolytic addition reaction of aldehydes to activated alkenes and subsequent reduction with hydride under continuous flow reaction conditions provides multisubstituted γ-lactones as mixtures of diastereomers.

A headspace solid-phase microextraction coupled to gas chromatography with mass spectrometry and flame ionization detection (HS-SPME-GC-MS/FID) method has been developed for quantifying the main volatiles of the Italian sparkling red wine Vernaccia di Serrapetrona, leading to establish that the divinylbenzene/carboxen/polydimethylsiloxane-coated (g...

Polyfunctionalized alkyl indole 2-carboxylates can be easily synthesized starting form -nitroacrylates and o-bromoanilines through an addition-elimination process followed by an intramolecular palladium-catalyzed Heck reaction.

The solvent-free acetylation of nitroalcohols (I) followed by elimination of acetic acid leads to desired β-nitroacrylates (II) in high yields.

We report, a new synthetic approach to beta-nitroacrylates by dehydration of the corresponding nitroalkanols, under fully heterogeneous conditions and with low resource consumption.

Substituted piperazines are important heterocycles possessing wide and important biological activities. Herein we report a new easy synthetic approach for preparation of alkyl 3-substituted 5-oxopiperazine-2-carboxylates using β-nitroacrylates as key starting materials. Graphical abstract

The reaction can also be conducted in THF.

The clam Anadara inaequivalvis (Bruguière) is a bivalve mollusc now populating several areas of the Mediterranean Sea seafloor where it competes with other molluscs harvested as food. In fact, even though Anadara inaequivalvis has valuable nutritional properties, it has no commercial value in European countries. The aim of this study was to evaluat...

The novel two-step protocol includes reaction of bromonitromethane with aldehydes and subsequent dehydration of the crude nitro alcohols.

Tosylates and mesylates were directly converted into the corresponding nitroalkanes, by their treatment with tetrabutylammonium nitrite (TBAN) under mild conditions.

The synthesis and reactivity of conjugated electron-deficient dienes and, particularly, their use in Diels-Alder reactions, remains a challenge in synthetic organic chemistry. The introduction of electron-withdrawing substituents on a conjugated dienic system allows the regiocontrolled synthesis of new cyclohexenes with a high level of functionaliz...

The photochemical synthesis of benzo[a]carbazoles from easily synthesizable 2‐aryl‐3‐(1‐tosylalkyl)indoles is presented. Irradiation of these substrates in polar aprotic solvents (acetone or THF) gives selectively the target products in satisfactory yields. This versatile and efficient procedure promises to be a useful alternative to the multistep...

The reaction of ylidene malononitriles with β-nitroacrylates, in Et3N/MeCN, affords the one-pot synthesis of a new class of penta-substituted, densely functionalized anilines in satisfactory to good overall yields. The method represents a very important improvement of the recent strategy for the preparation of anilines from conjugated nitroalkenes.

A base-free, recyclable approach for the conjugate addition of aliphatic nitro compounds to enones to give γ-nitro ketones is presented. Reactions are carried out in an ionic liquid with a basic anionic moiety, such as BmimNTf2, as the solvent, under mild conditions (25 °C for 24 h). The IL medium could be recycled several times without any appreci...

Phosphonium ionic liquids exchanged with bicarbonate and methylcarbonate anions (CILs) exhibit catalytic performances comparable to those of sterically hindered (non nucleophilic) organosuperbases such as DBU. At 25-50 degrees C, under solventless conditions, CILs efficiently catalyze the Henry addition of different aldehydes and ketones to nitroal...

The keto-enol tautomerism of some cyclic 2-nitroalkanones was studied in cyclohexane. Keto-enol equilibrium constants, K(T), at 25 °C were obtained from (1)H NMR spectra. The relative enol content for the investigated ketones as a function of ring size decreases in the order 6 > 7 > 11 > 12 > 15. This trend apparently is different from that observe...

The work-up step is merely a filtration of the crude reaction mixture and a subsequent evaporation of volatile compounds.

The keto-enol tautomerism of some cyclic 2-nitroalkanones was studied in cyclohexane. Keto-enol equilibrium constants, K(T), at 25 °C were obtained from (1)H NMR spectra. The relative enol content for the investigated ketones as a function of ring size decreases in the order 6 > 7 > 11 > 12 > 15. This trend apparently is different from that observe...

The reaction of β-nitroacrylates with β-enaminones, at room temperature and under solvent- and promoter-free conditions, affords the one-pot synthesis of polyfunctionalized pyrroles in high yields.

An innovative procedure under mild conditions is presented.

This work was aimed at preparing o-(6′-nitrocyclohex-3′-en- 1′-yl)phenol and tetrahydro-6H-benzo[c]chromen-6-ol derivatives in three steps starting from salicylaldehydes. Initially 3-acetylcoumarins were prepared in the absence of solvent using a solid base catalyst such as PS-TBD. In the second step, the Diels-Alder reactions of 3-nitrocoumarins a...

Italy Clam Scapharca inaequivalvis is a bivalve mollusk of Indo-Pacific origin, currently living also in the Adriatic Sea. Despite its content of valuable nutrients, 1 it is not much appreciated as food in Mediterranean area and thus fishermen must pick it out from the clam Camelea gallina. 2 Some of its precious nutrients are polyunsaturated fatty...

A variety of alpha,beta-unsaturated ketones can be easily converted, at room temperature, into beta-nitro ketones by nitration with solid supported nitrite (SSN) and in the presence of acetic acid and cyclopentyl methyl ether.

The reaction of beta-nitroacrylates with pyrroles, under solvent- and catalyst-free conditions, allows the formation of Friedel Crafts adducts which, after in situ treatment with Amberlyst 15 in isopropyl alcohol under reflux, provide polysubstituted indoles, via a benzannulation reaction, in a one-pot process.

The carbanion stabilizing effect of the nitro group makes nitroalkanes ideal reagents in carbon-carbon bond formation. Once introduced in a molecular framework, the nitro group is amenable to further transformations including reduction to primary amines. The aim of this review is to explore the utilization of nitroalkanes as effective substrates fo...

Reaction of sulfonylindoles with protected β-nitro ketones affords the corresponding 3-(2-nitroalkyl)indoles that, under acidic conditions, undergo a sequence of cascade processes finally leading to unsymmetrical 1,4-disubstituted carbazoles.

JandaJel, with its greater spacing between the linear polymeric chains compared to that of polystyrene matrices, is a very efficient support for improving the catalytic efficiency of TBD under SolFC.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The regio- and diastereoselective syntheses of several nitro-functionalized α,β-unsaturated esters such as (III) or (IX)/(X) and — at higher temperatures — butadienecarboxylates (IV)/(V) proceed under eco-friendly conditions, using the eco-compatible solvent ethyl acetate and a solid and reusable promoter.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A highly efficient conversion of β-nitrostyrenes into a new kind of functionalized N-alkoxy-2-hydroxypiperidine in two steps was developed, giving excellent yields and diastereoselectivity. The prepared compounds are the first examples of N-alkoxy-2-hydroxypiperidines. The synthetic approach involved the conjugate addition of alkoxyamines to β-nitr...

The procedure affords the target compounds in moderate to good yield and renders possible an easy introduction of substituents in positions 2 and 5.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

The nitroaldol reaction of ketal-functionalized nitroalkanes with alpha-oxoaldehydes, promoted by Amberlyst A21, followed by acidic treatment (Amberlyst 15) of the obtained nitroalkanol, leads to the formation of 2,5-disubstituted furans in good yields. The procedure was successfully applied to the total synthesis of 1-benzyl-3-(5'-hydroxymethyl-2'...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A splitless injection GC-FID method for determining mineral paraffins in food was set up. The method has been developed on vegetable oils and subsequently adjusted and applied to dried fruits, a food matrix not yet investigated from this point of view. The method avoids the saponification step foreseeing only a clean-up on silica gel SPE, and allow...

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.