Synthesis of 5‐Iodo‐4H‐1, 3‐oxazine‐4‐ones Through a [3+3] Reaction of Amides and Propiolates Induced by N‐Iodosuccinimide (NIS) and Cu(CF3SO3)2. Issue 12 (18th March 2015)

• Record Type: Journal Article
• Authors: Li, Chen; Liu, Nan; Qi, Qing‐Rong; Chen, Yue; He, Ling
• Is Part Of: European journal of organic chemistry. Issue 12(2015)
• Page Start: 2585
• Page End: 2589
• Publication Date: 2015-03-18
• Subjects: Synthetic methods -- Nitrogen heterocycles -- Cyclization -- ­Amides -- Alk­ynes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500015
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A series of novel trisubstituted 5‐iodo‐4 H ‐1, 3‐oxazine‐4‐ones were prepared in moderate to excellent yields induced by NIS and Cu(CF3 SO3 )2 through a [3+3] reaction of amides and propiolates. The reaction proceeds in a one‐pot manner under mild conditions and gives rise to a new strategy for the formation of trisubstituted 5‐iodo‐4 H ‐1, 3‐oxazine‐4‐ones and their derivatives. Abstract : A mild, one‐pot procedure to access 5‐iodo‐4 H ‐1, 3‐oxazine‐4‐ones has been developed. The reaction involves an N‐iodosuccinimide and Cu(CF3 SO3 )2 induced [3+3] reaction of amides and propiolates. The products are formed in moderate to excellent yields and their further derivatization through cross‐coupling reactions is reported.