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A Metal-catalyzed tandem 1,4-benzodiazepine synthesis based on two hydrogen-transfer reactions

Jumde, Varsha R. and Cini, Elena and Porcheddu, Andrea and Taddei, Maurizio (2015) A Metal-catalyzed tandem 1,4-benzodiazepine synthesis based on two hydrogen-transfer reactions. European Journal of Organic Chemistry, Vol. 2015 (5), p. 1068-1074. eISSN 1099-0690. Article.

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DOI: 10.1002/ejoc.201403261

Abstract

Starting from 2-aminobenzyl alcohols and 1,2-amino alcohols, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepines (TH-BDZ) can be prepared through a one-pot ruthenium-catalyzed reaction encompassing two consecutive borrowing hydrogen cycles. First, benzyl alcohol oxidation, condensation with the amino alcohol, and imine reduction occurs. This is followed by oxidation of the other alcohol functionality and reductive cyclocondensation to give the TH-BDZ derivatives. A single catalyst does the entire job, with two molecules of water being the only waste product. Many new substituted 2,3,4,5-tetrahydro-1H-1,4-benzodiazepines have been prepared to demonstrate the versatility of this method, which can be used for the preparation of privileged scaffolds for drug discovery.

Item Type:Article
ID Code:11006
Status:Published
Refereed:Yes
Uncontrolled Keywords:Hydrogen transfer, homogeneous catalysis, ruthenium, cyclization, domino reactions
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:001 Università di Sassari > 01-a Nuovi Dipartimenti dal 2012 > Chimica e Farmacia
Publisher:Wiley
eISSN:1099-0690
Deposited On:11 Jun 2015 12:43

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