Rocio gamez montaño

Universidad de Guanajuato · Department of Chemistry

A facile and rapid synthesis of a family of new hybrid system 1,5-disusbtituted 1H-tetrazol-5yl 4,5-dihydro [1,2,3]triazolo[1,5-a]pyrazin-6-ones in moderate yields is described. Compounds were synthetized by a high-order multicomponent reaction (MCR) to give N-acylated 1,5-disubstituted tetrazoles followed, without chromatographic purification, by...

An efficient iodine(III)‐based protocol for the chlorination and catalytic nitration of N‐tosyl anilines as well as the proposed reaction mechanism is described. The synergistic combination of the commercially available [bis(trifluoroacetoxy)iodo]benzene (PIFA) with AlCl3, or (PhIO)n with Al(NO3)3, allowed the electrophilic introduction of the chlo...

Zygomycetes are ubiquitous saprophytes in natural environments which transform organic matter. Some zygomycetes of gender Mucor have attracted interest in health sector. Due to its ability as opportunistic microorganisms infecting immuno-compromised people and to the few available pharmacological treatments, the mucormycosis is receiving worldwide...

The first, rapid, and inexpensive mechanochemical Ugi four-component reaction (MC-Ugi-4CR) has been developed for the sustainable synthesis of new dipeptides like products in high yields under mild, solvent-, catalyst-, and...

The initial results on a novel procedure for the synthesis of benzo [b] carbazols via gold (I)-catalyzed tandem cyclization/Migration/cyclization is described. The procedure allowed the access to a highly functionalized benzo [b] carbazols in a one-pot process starting from tertiary anilines. The mechanism of this reaction by using gold (I) catalys...

A series of ten 1,5-disubstituted-1H-tetrazoles (1,5-DS-T) were synthesized via Ugi-azide isocyanide-based multicomponent reactions (IMCR) in low to good yields (30–85%), using propargyl amine or 2-azidobenzaldehyde as a component, and using ultrasound irradiation (USI) as an alternative energy source. 1,5-DS-T are useful heterocyclic moieties, pre...

The initial results on a novel procedure for the synthesis of benzo[b]carbazols via gold(I)- catalyzed tandem cyclization/Migration/cyclization is described. The procedure allowed the access to a highly functionalized benzo[b]carbazols in a one-pot process starting from tertiary anilines. The mechanism of this reaction by using gold(I) catalysis, i...

A series of epoxyisoindolinones were synthesized by microwave-assisted post-IMCR transformation-based domino strategy via the Ugi-4CR/Intramolecular-Diels-Alder (U-4CR/IMDA) sequence under mild, solvent-, catalyst-free ecofriendly conditions, and orthogonal-bifunctional components. Epoxyisoindolinones are a privileged core of high interest in medic...

A novel strategy via the triple process (multicomponent reactions (MCR)-domino)/tandem was developed for the synthesis of restricted and constrained bis-1,2,3-triazole-linked pyrrolo[3,4-b]pyridine peptidomimetics dimers in overall yields of 20–55%. This strategy allows the construction of six heterocycles in two stages of the reaction.

In the presence of a catalytic amount of Pd(OAc)2 and XantPhos, the three-component reaction of ynones, imines, and aryl iodides affords fully substituted alkylidene-furan-3(2H)-ones via a sequence of the Mannich reaction followed by chemo- and regioselective oxypalladation and reductive elimination. One carbon-oxygen and two carbon-carbon bonds ar...

Iodine(III)-based reagents has been broadly used in oxidative reactions for the structural functionalization with several functional groups. Among the more relevant and useful synthetic transformations using these hypervalent γ ³ -reagents, it can be found the fluorination, chlorination, bromination as well as the iodination protocols. Herein, we p...

The Ugi reaction of 2-nitrobenzoic acid derivatives has been used for a Diversity Oriented Synthesis of complex isoindolinones via a SNAr reaction involving the peptidyl position. When the cyclization is triggered by strong bases such as potassium tert-butylate, the SNAr reaction is followed by a deamidification/oxydation sequence leading to 2-hydr...

6-Triazolylmethyl-pyrrolo[3,4-b]pyridin-5-one tris-heterocycles were synthesized in 43–57% overall yields. The two-stage synthesis involved a cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization) followed by a copper-assisted alkyne-azide [3+2] cycloaddition (CuAAC). This efficient and convergent strategy proceeded via complex termina...

Six novel imidazo[1,2-a]pyridines were synthesized by Groebke–Blackburn–Bienaymé reactions (GBBRs) under eco-friendly conditions (10 mol% ammonium chloride catalyst in EtOH at room temperature) with moderate to good yields (76–44%) using 2-isocyano-1-morpholino-3-phenylpropan-1-one. This is the first successful use of this type of α-isocyanoacetami...

An efficient Microwave (MW)-assisted synthesis of eight new 6-nitrilmethyl-pyrrolo[3,4-b]pyridin-5-ones via a domino process: aza Diels–Alder/N-acylation/aromatization (dehydration–decarboxylation) from their corresponding 2-aminonitrile-oxazoles and maleic anhydride are described. The use of MW as a heat source and scandium (III) triflate as a cat...

Green and an improved ultrasound assisted synthesis of 1-substituted 1H-1,2,3,4-tetrazoles via novel isocyanide based multicomponent click reaction (IMCCR) under mild, solvent, catalyst and column-free conditions have been developed. This new,...

A new, efficient, green, endogenous water-triggered, solvent- and catalyst-free ultrasound-assisted one-pot Groebke–Blackburn–Bienaymé reaction/SNAr/ring-chain azido-tautomerization strategy to synthesize bound-type fused bis-heterocycles imidazo or benzo[d]imidazo[2,1-b]thiazoles and 1,5-disubstituted tetrazole (1,5-DsT) containing quinoline moiet...

Six novel tris-heterocycles 1′-tetrazolylmethyl-spiro[pyrrolidine-3,3′-oxindoles] were synthesized in 39-82% yields in two experimental steps: (i) a one-pot Ugi-azide/Pictet-Spengler process coupled to (ii) a one-pot oxidative spiro-rearrangement. The synthesized polyheterocycles could be used for further in vitro studies because they contain moiet...

A docking studies of a set of several 1,5-disubstituted tetrazoles (1,5-DS-T) compounds to find potential inhibitors of the Abelson tyrosine-protein kinase (ABL kinase) and the mutated ABL kinase T315I were conducted by using Lamarckian genetic algorithms as search algorithms in Autodock4. Bayesian calculations were performed, and specificity (Sp)...

A novel, sustainable, endogenous water-triggered, environmentally friendly, high substrate scope, efficient, solvent-free and catalystfree Ugi-azide based method for the synthesis of 1,5-disubstituted tetrazoles is described.

A series of sixteen new 2-julolidin-imidazo[1,2-a]pyridine bound-type bis-heterocycles were synthesized in good to excellent yields (61–98%) via an MW-assisted Groebke–Blackburn–Bienayme (GBB) reaction. Then, experimental studies were conducted to determine the luminescence properties of these compounds. Various high quantum yields were found. In f...

A series of fifteen 2-tetrazolylmethyl-isoindolin-1-one linked-type bis-heterocycles were synthesized in 10–76% yields under mild conditions via a one-pot Ugi-azide/(N-acylation/exo-Diels–Alder)/dehydration process from furan-2-ylmethanamine, aldehydes, isocyanides, azidotrimethylsilane, and maleic anhydride. Density functional theory calculations...

A series of five novel 1-tetrazolyl-1,2,3,4-tetrahydroisoquinolines were synthesized in moderate yields (29-60%) by a two-step process. The first one involved a NH-CH2 bond oxidation of the 1,2,3,4-tetrahydroisoquinoline to give the corresponding imine using IBX as oxidant. The second step was an oxidative Ugi-azide reaction using 3,4-dihydroisoqui...

A series of seven new 2-tetrazolylmethyl-tetrahydro-1H-beta-carboline methane-linked bis-heterocycles including their fluorine-containing analogs were synthesized in good to excellent yields (74-97%) via one pot Ugi-azide / Pictet-Spengler strategy under mild thermal conditions. One intermediate (Ugi-azide product) was isolated and fully characteri...

The trimethylsilyl chloride promoted title reaction may be intercepted with different nucleophiles offering access to interesting adducts.

The title tetrazoles (30 examples) may exhibit cytotoxicity and/or tyrosine-kinase inhibitory properties because of their structural similarities with potent cancer drugs such as imatinib.

A series of 18 3-tetrazolyl-tetrazolo[1,5-a]quinolines were synthesized in 21-90% yields via a novel one-pot Ugi-azide/SNAr/ring-chain azido-tautomerization process. We report also the synthesis of 10 3-imidazo[1,2-a]pyridin-tetrazolo[1,5-a]quinolines in 28-94% yields via a novel one-pot Groebke-Blackburn-Bienaymé/SNAr/ring-chain azido-tautomerizat...

Title compounds (VI) are conveniently synthesized in two steps via a multicomponent reaction affording Ugi products (V) followed by Pd-catalyzed aerobic oxidative cyclization.

This is the first report describing the formation of the title compounds (VII) in which the precursors (VI) are prepared in a one-pot manner by a multicomponent reaction.

Trimethylsilyl chloride is an efficient activating agent for azines in isocyanide-based reactions, which then proceed through a key insertion of the isocyanide into a N-Si bond. The reaction is initiated by N activation of the azine, followed by nucleophilic attack of an isocyanide in a Reissert-type process. Finally, a second equivalent of the sam...

Trimethylsilyl chloride is an efficient activating agent for azines in isocyanide-based reactions, which then proceed through a key insertion of the isocyanide into a N−Si bond. The reaction is initiated by N activation of the azine, followed by nucleophilic attack of an isocyanide in a Reissert-type process. Finally, a second equivalent of the sam...

Density Functional Theory (DFT) based calculations were performed at the PCM (toluene)-M06-2X/6-311+G(d) // M06-2X/6-31G(d) level of theory to rationalize the construction of the pyrrolo[3,4-b]pyridin-5-one core from a variety of 5-aminooxazoles and maleic anhydride because there are two possible reaction pathways; A = N-acylation / aza Diels-Alder...

A series of twenty three novel unsymmetrical bis-heterocycles having either imidazo[2,1-b]thiazole or benzo[d]imidazo[2,1-b]thiazole frameworks bound with chromone, quinoline or julolidine were synthesized in good to excellent yields (82–97%) by an acid-free Groebke-Blackburn-Bienaymé reaction (GBBR) under microwave–heating conditions. Additionally...

A series of nine new 3-acetamide-azepino[4,5-b]indol-4-ones were synthesized in two steps: i) multicomponent reaction (Ugi-4CR / SN2) and ii) free radical-mediated cyclization. These compounds, along with their tetrazole-based analogs, were studied in vitro to assess their binding with the 5-hydroxytryptamine type 6 receptor (5-Ht6R). The 3-acetami...

Novel tetrahydroindeno[1,2-b]pyrrolidineswereconveniently prepared in moderate to good yields via a sequential Ugi multicomponent reaction or Staudinger/aza-Wittig/Ugi combination, followed by the palladium-catalyzed aerobic oxidative cyclization of the resulting Ugi adducts.

A rapid and efficient synthesis of a series of (±)-nuevamine, (±)-lennoxamine and magallanesine aza analogues is described. The synthetic strategy involves Ugi-3CR and two further condensation processes, aza-Diels-Alder cycloaddition and the Pomeranz-Fritsch reaction. The variation of the chain-size in aldehyde moieties provided structural diversit...

The development of efficient methods for the synthesis of heterocyclic compounds is always of great importance for chemists. In this perspective, we describe a general approach for the synthesis of functionalized heterocyclic via Ugi MCR followed by intramolecular ylide initiated Michael reaction, In this case, the reaction proceeds via in-situ gen...

In this work, we describe the synthesis of novel triazolylmethyl-pyrrolo[3,4-b]pyridin-5-ones by a sequence: Ugi-3CR / aza Diels-Alder / Click. There are several reports about pyrrolo[3,4-b]pyridin-5-ones related to various type of biological activity.We reported two methodologies for synthesizing series of novel pyrrolo[3,4-b]pyridine-5-ones using...

Ugi adducts of cyanoacetic acid and aromatic aldehydes are readily cyclized under basic conditions leading to one-pot formation of aminopyrrolinone derivatives.

In vitro studies to fourteen previously synthesized chromone-tetrazoles and four novel fluorine-containing analogs were conducted against pathogenic protozoan (Entamoeba histolytica), pathogenic bacteria (Pseudomonas aeruginosa, and Staphylococcus aureus), and human fungal pathogens (Sporothrix schenckii, Candida albicans, and Candida tropicalis),...

Abstract The synthesis of four novel benzo-fused spiropiperidines and the lead σ-1 receptor ligand L-687384 through a xanthate-mediated free radical spirocyclization as key step is described. Furthermore, the key free radical-based cyclization was computationally studied by means of the density functional theory approach at the UB3LYP/6-311+G(d) le...

Based on in vitro studies of twelve newly-synthesized 1-acetamide-5-methoxy-2-oxindoles as 5-Ht7 receptor ligands, Structure Affinity Relationship (SAR) and Quantitative Structure Affinity Relationship model (QSAR) are provided. Also, a ligand-based pharmacophore model is proposed through molecular docking techniques and Nucleus Independent Chemica...

A series of five novel bis-1,5-disubstituted-1H-tetrazoles (bis-1,5-DS-1H-T) were quickly prepared by a catalyst-free Ugi-azide repetitive process from easily accessible starting materials in excellent yields, either at room temperature (88%-95%) or using mild MW-heating conditions (80%-91%). These molecules may have a wide range of applications, s...

A series of nine novel imidazo[1,2-a]pyridin-chromones and nine novel imidazo[1,2-a]pyridin-6-fluorochromones were synthesized in good to excellent yields by a MW assisted Groebke-Blackburn-Bienaymé reaction (GBB) under mild thermal and acidic conditions. Additionally, optimized geometries for the two non-prepared 5-bromoimidazo[1,2-a]pyridin-chrom...

A series of twelve novel 1-acetamide-5-methoxy-2-oxindoles were prepared in moderate to good yields (30–88%) by an Ugi-SN2 one pot process with a xanthate mediated free radical cyclization. Additionally, Density Functional Theory (DFT) based calculations were performed at UB3LYP/6-311G(d) level in order to rationalize the energy profile of the xant...

A series of novel 2-tetrazolylmethyl-2,3,4,9-tetrahydro-1H--carbolines were prepared in good to excellent overall yields by an efficient MW-assisted one-pot Ugi-azide/Pictet-Spengler process. This work describes the first synthesis of compounds including both 1,5-disubstituted 1H-tetrazole and 2,3,4,9-tetrahydro-1H--carboline heterocyclic systems.

A new arylation of isocyanides with diazonium salts via an aryl nitrilium species as key intermediate is developed.

A series of eighteen novel 1,5-disubstituted-1H-tetrazoles has been prepared with moderate to good overall yields using an Ugi-azide reaction as key step under mild conditions. Tetrazoles are heterocyclic systems present in several synthetic products which have privileged biological activity. Therefore, in this paper we describe the synthesis of no...

A series of nine novel 3-tetrazolylmethyl-azepino[4,5-b]indol-4-ones were prepared in moderate to good overall yields in only two reaction steps. The first step consisted of a one-pot sequential process of an Ugi-azide multicomponent reaction, N-acylation and SN2 to give the xanthates. The second step was an intramolecular cyclization under free ra...

Mumm's the word: The title reaction can be performed by the addition of isocyanides to benzenediazonium salts in the presence of sodium or potassium carboxylates. The reaction involves nitrilium intermediates which may be trapped by water or carboxylic acids to form amides and imides, respectively, after Mumm rearrangement.

A one-pot procedure including Ugi three-component reaction, aza-Diels—Alder cycloaddition and aromatization provides key intermediates (V).

A series of nuevamine aza-analogues were prepared in moderate to good yields in two reaction steps. The synthetic strategy involves an isonitrile-based multicomponent reaction, including an aza-Diels-Alder cycloaddition and Pictet-Spengler reaction as postcondensation.

Flavones were directly alkylated at the C-3 position in moderate yields using a xanthate-based oxidative radical addition procedure. This methodology is a suitable synthetic tool for the direct substitution of the vinylic and unactivated C-H bond of the C ring of the flavone by an alkyl functionality under neutral conditions.

A series of tetrahydroisoquinolin-pyrrolopyridinones were prepared from an easily accessible aldehyde, a commercially available amine, a readily isolable isonitrile, and maleic anhydride via a triple process: Ugi-3CR–aza Diels–Alder/S-oxidation/Pummerer. The combination of a multicomponent Ugi-type reaction with other post-functionalization process...

An efficient and convenient access to 2-tert-butylisoindolin-1-ones via an oxidative radical cyclization process from stable carbamoylxanthates, derived from secondary tert-butylamines, is described. The proposed mechanism for this transformation involves, the generation of a carbamoyl radical, its cyclization to the aromatic system, and the dilaur...

By use of a sequential combination of Ugi reaction and microwave-promoted radical spirocyclization, an efficient protocol for the preparation of five- and six-membered spirolactams is developed.

Oxidative cleavage and cyclization cascades of N-aryl peptides have been achieved under palladium catalysis with air as the sole stoichiometric oxidant.

An efficient xanthate-based method for the preparation of azaspirocyclic cyclohexadienones via an ipso oxidative radical cyclization of p-oxygenated N-benzylacetamides and N-phenetylacetamide is described.

The reaction of aldehydes and ketones, including aliphatic and aromatic ones, with amides of α-isocyano-β-phenylpropionic acid in toluene in the presence of lithium bromide gives 2,4,5-trisubstituted oxazoles in good to excellent yield. Protected chiral α-amino aldehydes participate in this reaction to give, after hydrolysis of the oxazoles, norsta...

From readily available allylamine, aldehyde and isocyanoacetamide, a three-component reaction followed by a Pummerer cyclization provided tetracyclic ring systems (6-7-5-6 and 6-6-5-6) in excellent overall yields.

Novel three-component domino processes to polyheterocycles are developed. Reaction of an allylamine, an aldehyde and an alpha -isocyanoacetamide in methanol at room temp. provides an efficient access to an oxa-bridged tricycle as a single diastereoisomer. In this one-pot process, one C-N, one C-O and three C-C bonds are formed with concomitant crea...

The first stereoselective synthesis of 1-aryl-2-benz[c]azepines is described using oxazolidines as chiral inducers.