Synthesis of thiazole, oxazole and heterocyclic ring-substituted 1,2-dioxanes

✍ Scribed by Michiharu Sakata; Yumi Shirakawa; Nobuhito Kamata; Yuko Sakaguchi; Hiroshi Nishino; Jie Ouyang; Kazu Kurosawa

• Book ID: 102342444
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2000
• Tongue: English
• Weight: 428 KB
• Volume: 37
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570370208

✦ Synopsis

Abstract

The reactions of 4‐bromoacetyl‐3‐methoxy‐3‐methyl‐6,6‐diphenyl‐1,2‐dioxane with thioureas or thioamides gave 3‐methoxy‐3‐methyl‐6,6‐diphenyl‐4‐(4‐thiazolyl)‐1,2‐dioxanes in 63–90% yields. The similar reaction of 4‐bromoacetyl‐3‐methoxy‐3‐methyl‐6,6‐diphenyl‐1,2‐dioxane with acetamide gave 3‐methoxy‐3‐methyl‐4‐(2‐methyl‐4‐oxazolyl)‐6,6‐diphenyl‐1,2‐dioxane in 39% yields. The reactions of 4‐bromoacetyl‐3‐methoxy‐3‐methyl‐6,6‐diphenyl‐1,2‐dioxane with 3‐alkyl‐4‐amino‐5‐mercaptot[1,2,4]triazoles yielded 3‐methoxy‐3‐methyl‐6,6‐diphenyl‐4‐[3‐(5‐alkyl[1,2,4]triazolo[3,4‐b]‐2,3‐dihydro‐6__H__‐[1,3,4]thiadiazinyl)]‐1,2‐dioxanes in moderate yields (43–46%).