1,4-thiazepines, 1,4-benzothiazepin-5-ones, and 1,4-benzothioxepin orthoamides via multicomponent reactions of isocyanides

Stefano Marcaccini; Daniel Miguel; Tomás Torroba; María García-Valverde

doi:10.1021/jo026614z

1,4-thiazepines, 1,4-benzothiazepin-5-ones, and 1,4-benzothioxepin orthoamides via multicomponent reactions of isocyanides

J Org Chem. 2003 Apr 18;68(8):3315-8. doi: 10.1021/jo026614z.

Authors

Stefano Marcaccini¹, Daniel Miguel, Tomás Torroba, María García-Valverde

Affiliation

¹ Dipartimento di Chimica Organica Ugo Schiff, Università di Firenze, 50019-Sesto Fiorentino, Florence, Italy.

PMID: 12688810
DOI: 10.1021/jo026614z

Abstract

The intramolecular Ugi four-component condensation between 6-oxo-4-thiacarboxylic acids, benzylamines, and cyclohexyl isocyanide gave hexahydro-1,4-thiazepin-5-ones and 1,4-benzothiazepin-5-ones, in some cases with high stereoselectivity, and the intramolecular Passerini three-component reaction, in the presence of catalytic amine, gave tetracyclic 1,4-benzothioxepin orthoamides.