Parallel synthesis of 4,5-dihydro-1H-1,4-benzodiazepine-2,3-diones

Citation
A. Nefzi et al., Parallel synthesis of 4,5-dihydro-1H-1,4-benzodiazepine-2,3-diones, TETRAHEDR L, 42(31), 2001, pp. 5141-5143
Citations number
18
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
31
Year of publication
2001
Pages
5141 - 5143
Database
ISI
SICI code
0040-4039(20010730)42:31<5141:PSO4>2.0.ZU;2-S
Abstract
An efficient strategy for the parallel solid-phase synthesis of 4,5-dihydro -1H-1,4-benzddiazepine-2,3-diones is described. The reductive alkylation of resin-bound primary amine with different substituted o-nitrobenzaldehydes generated a secondary amine, which was treated further with methyl chloroox oacetate. The nitro group was reduced with tin(II) chloride. During the ove rnight reduction, an in situ intramolecular cyclization occurred to provide , following HF cleavage, the desired 4,5-dihydro-1H-1,4-benzodiazepine-2,3- dione. (C) 2001 Elsevier Science Ltd. All rights reserved.