The synthesis of hexahydrooxoepithiopyridinedicarboximides by the reaction of thioamides with N-substituted maleimides

✍ Scribed by Toshio Takido; Sachiko Tamura; Kenji Sato; Haruo Kamijo; Toshikatsu Nakazawa; Manabu Seno; Tadashi Hata

• Book ID: 102892849
• Publisher: Journal of Heterocyclic Chemistry
• Year: 1998
• Tongue: English
• Weight: 587 KB
• Volume: 35
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570350229

✦ Synopsis

Abstract

The synthesis of hexahydrooxoepithiopyridinedicarboxyimide (5: X~2~ = N‐Ph) by the reaction of thioamides 1 with N‐substituted maleimide (2a) was examined. The reaction of primary thioamides, such as thiobenzamide and p‐toluthioamide with N‐phenylmaleimide gives compounds 5 together with corresponding 4‐hydroxy‐1,3‐thiazoles 4. However, a similar reaction of secondary thioamides, such as N‐methylthioacetamide, thiobenzanilide, with N‐phenylmaleimide did not provide compounds 5 without addition of acid. The reaction pathway and the configuration of 5 were also investigated.