A Metal‐Catalyzed Tandem 1, 4‐Benzodiazepine Synthesis Based on Two Hydrogen‐Transfer Reactions. Issue 5 (22nd December 2014)

• Record Type: Journal Article
• Authors: Jumde, Varsha R.; Cini, Elena; Porcheddu, Andrea; Taddei, Maurizio
• Is Part Of: European journal of organic chemistry. Issue 5(2015)
• Page Start: 1068
• Page End: 1074
• Publication Date: 2014-12-22
• Subjects: Hydrogen transfer -- Homogeneous catalysis -- Ruthenium -- Cyclization -- Domino reactions; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201403261
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Starting from 2‐aminobenzyl alcohols and 1, 2‐amino alcohols, 2, 3, 4, 5‐tetrahydro‐1 H ‐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‐1 H ‐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. Abstract : Two consecutive Ru‐catalyzed borrowing hydrogen processes offer an efficient method for benzodiazepine synthesis.