Efficient p-Amino Benzoic Acid Catalyzed Eco-friendly Synthesis of 1,5-benzodiazepines among Various Amino Acids under Solvent Free Conditions

Sugar‐based Morita–Baylis–Hillman (MBH) acetates easily obtained from commercially available D‐glucal underwent rapid reaction with 1,2‐benzenediamines to give, in good yields, a series of enantiomerically pure tricyclic pyrano‐fused 1,5‐benzodiazepines with multiple points of diversity, which could serve as potential drug scaffolds. The driving force behind this reaction seemed to be the high stability associated with the conjugated tricyclic system. The reaction involved an unprecedented amine–carbonyl condensation/[3,3]‐sigmatropic rearrangement/cyclization cascade.

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Conjugation‐Driven Cascade Approach to Enantiopure Pyrano‐Fused 1,5‐Benzodiazepines by Tandem Condensation/[3,3]‐Sigmatropic Rearrangement/Aza‐Michael Addition–Elimination

Husain

Saquib

Shaw

2013

Eur J Org Chem

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Sulfanilic acid: a versatile and efficient catalyst among various organoacids screened for the synthesis of 1-amidoalkyl-2-naphthols under solvent-free condition

Singh

Duvedi

et al. 2014

Res Chem Intermed

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Multicomponent Catalytic Synthesis of 1,5-Benzodiazepines: An Update

Singh

Sharda

Sharma³

et al. 2020

MROC

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1,5-Benzodiazepines are considered some of the most vital classes of heterocyclic compounds due to their amazing biological and varied pharmacological activities. They are regarded as privileged structures and therefore have been striking synthetic targets for organic and medicinal chemists over the last decade. This results in the exploration of various silica supported catalysts, Lewis acids, organoacids, magnetic nanoparticles and other miscellaneous catalysts that have been investigated till date for an efficient and green synthesis of 1,5-benzodiazepine and its derivatives. The current review article primarily covers the one-pot green chemical synthesis of 1,5- benzodiazepines using various novel catalysts. The main motive of this review is the assessment of the literature on various catalysts along with their yield, reaction condition, and mechanism of action. In the end, the entire catalysts are structured systematically into various Lewis acids, Bronsted organoacids, supported catalysts, nanocatalysts, and miscellaneous catalysts and are presented in the form of tables for quick ‘at a glance’ study of catalysts, their reaction condition, time taken, etc.

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Efficient p-Amino Benzoic Acid Catalyzed Eco-friendly Synthesis of 1,5-benzodiazepines among Various Amino Acids under Solvent Free Conditions

Cited by 4 publications

References 9 publications

Conjugation‐Driven Cascade Approach to Enantiopure Pyrano‐Fused 1,5‐Benzodiazepines by Tandem Condensation/[3,3]‐Sigmatropic Rearrangement/Aza‐Michael Addition–Elimination

Conjugation‐Driven Cascade Approach to Enantiopure Pyrano‐Fused 1,5‐Benzodiazepines by Tandem Condensation/[3,3]‐Sigmatropic Rearrangement/Aza‐Michael Addition–Elimination

Sulfanilic acid: a versatile and efficient catalyst among various organoacids screened for the synthesis of 1-amidoalkyl-2-naphthols under solvent-free condition

Multicomponent Catalytic Synthesis of 1,5-Benzodiazepines: An Update

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