Novel syntheses of tetrahydrobenzodiazepines and dihydropyrazines via isocyanide-based multicomponent reactions of diamines

Ahmad Shaabani; Ali Maleki; Fatemeh Hajishaabanha; Hamid Mofakham; Mozhdeh Seyyedhamzeh; Mojtaba Mahyari; Seik Weng Ng

doi:10.1021/cc900125a

Novel syntheses of tetrahydrobenzodiazepines and dihydropyrazines via isocyanide-based multicomponent reactions of diamines

J Comb Chem. 2010 Jan-Feb;12(1):186-90. doi: 10.1021/cc900125a.

Authors

Ahmad Shaabani¹, Ali Maleki, Fatemeh Hajishaabanha, Hamid Mofakham, Mozhdeh Seyyedhamzeh, Mojtaba Mahyari, Seik Weng Ng

Affiliation

¹ Department of Chemistry, Shahid Beheshti University, Tehran, Iran. a-shaabani@cc.sbu.ac.ir

PMID: 19928912
DOI: 10.1021/cc900125a

Abstract

In this work, two novel isocyanide-based multicomponent reactions of 1,2-diamine compounds with diketene have been developed as efficient strategies for the synthesis of 2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepine-2-carboxamides with regiochemical control and 1,6-dihydropyrazine-2,3-dicarbonitriles in good to excellent yields at ambient temperature.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amines / chemistry*
Benzodiazepines / chemical synthesis*
Benzodiazepines / chemistry
Combinatorial Chemistry Techniques / methods*
Cyanides / chemistry*
Molecular Structure
Pyrazines / chemical synthesis*
Pyrazines / chemistry
Stereoisomerism

Substances

Amines
Cyanides
Pyrazines
Benzodiazepines