Rhodium‐Catalyzed Synthesis of 2, 5‐Epoxybenzo[f][1, 4]oxazepines by Tandem Reaction of 1‐Sulfonyl‐1, 2, 3‐triazoles and Salicylaldehydes. Issue 29 (11th September 2015)

• Record Type: Journal Article
• Authors: Shi, Yinping; Yu, Xing; Li, Chuan‐Ying
• Is Part Of: European journal of organic chemistry. Issue 29(2015)
• Page Start: 6429
• Page End: 6433
• Publication Date: 2015-09-11
• Subjects: Synthetic methods -- Homogeneous catalysis -- Carbenes -- Nitrogen heterocycles -- Rhodium -- Cyclization; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500912
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: Readily available 1‐sulfonyl‐1, 2, 3‐triazoles were converted into α‐imino carbenes in the presence of catalytic amounts of rhodium(II) salts. The carbenes underwent a tandem reaction with salicylaldehydes to provide a series of functionalized 2, 5‐epoxybenzo[ f ][1, 4]oxazepines in high yields. Abstract : A novel protocol for the synthesis of 2, 5‐epoxybenzo[ f ][1, 4]oxazepines is developed. The complicated ring system can be constructed from readily available N ‐sulfonyl‐1, 2, 3‐triazoles and salicylaldehyde derivatives in a one‐pot procedure. Many valuable functional groups are well tolerated in this transformation. [Rh2 (piv)4 ] = dirhodium(II) tetrapivalate.