A Study of the Reactions of 3‐Bromopropenals with Anilines for the Synthesis of α‐Bromo Enaminones. Issue 21 (7th September 2021)

• Record Type: Journal Article
• Authors: Suresh, Sundaram; Bhimrao Patil, Prakash; Yu, Pao‐Hsing; Fang, Chia‐Chi; Weng, Yin‐Zhi; Kavala, Veerababurao; Yao, Ching‐Fa
• Is Part Of: Advanced synthesis & catalysis. Volume 363:Issue 21(2021)
• Page Start: 4915
• Page End: 4925
• Publication Date: 2021-09-07
• Subjects: One-pot synthesis -- α-bromo enaminones -- 3-bromopropenals -- anilines -- dimethyl sulfoxide; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202100779
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A one‐pot strategy for the synthesis of α ‐bromo enaminones is reported. The reactions proceed via the p ‐toluenesulfonic acid monohydrate (TsOH ⋅ H2 O) catalyzed reactions of 3‐bromopropenals with anilines in dimethyl sulfoxide (DMSO) and does not require an external brominating agent. The chemoselective 1, 2‐addition was accomplished by employing aniline with a sterically hindered electron‐withdrawing group attached at the ortho ‐position. In addition, the reactions involving other aniline derivatives as nucleophiles have resulted in minor yields of 1, 4‐addition product. The 3‐bromopropenals showed a diverse range of reactivities with aniline derivatives. Abstract :