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Synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics: Oxidation of cyclic secondary amine with TPAP

✍ Scribed by Ahmed Kamal; Philip W Howard; B.S Narayan Reddy; B.S Praveen Reddy; David E Thurston

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 384 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)00033-1

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✦ Synopsis

A facile procedure for the preparation of the imine form of the pyrrolo[2,1-cl[l,4]benzodiazepine ring system by the oxidation of cyclic secondary amine with catalytic amounts of tetra-n-propylammoniam perruthenate (TPAP) and N-methylmorpholine N-oxide (NMO) as a co-oxidant is described. This oxidative method is devoid of side-products and is thus a significant improvement over the Swern oxidation previously reported.

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