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.

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

PORCHEDDU, ANDREA;
2015

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.
Cyclization; Domino reactions; Homogeneous catalysis; Hydrogen transfer; Ruthenium; Organic Chemistry; Physical and Theoretical Chemistry
File in questo prodotto:
File Dimensione Formato  
A Metal-Catalyzed Tandem.pdf

Solo gestori archivio

Tipologia: versione editoriale
Dimensione 804.66 kB
Formato Adobe PDF
804.66 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11584/143950
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 27
  • ???jsp.display-item.citation.isi??? 26
social impact