Synthesis of 3-Substituted Tetrahydrofuran and 4-Substituted Tetrahydropyran Derivatives by Cyclization of Dicarboxylic Acids with InBr3/TMDS

• Published in: European journal of organic chemistry Vol. 2012; no. 25; pp. 4689 - 4693
• Main Authors: Pehlivan, Leyla, Métay, Estelle, Delbrayelle, Dominique, Mignani, Gérard, Lemaire, Marc
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.09.2012; WILEY‐VCH Verlag; Wiley; Wiley-VCH; Wiley Subscription Services, Inc; Wiley-VCH Verlag
• Subjects: Acids; Carboxylic acids; Chemical Sciences; Chemistry; Chemistry, Organic; Cyclization; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Indium; Organic chemistry; Oxygen heterocycles; Physical Sciences; Preparations and properties; Reduction; Science & Technology; SYSTEM; Reduction; Cyclization; Oxygen heterocycles; RADICAL CYCLIZATION; Carboxylic acids; CYCLIC ETHERS; Indium; Ether; Furan derivatives; Pyran derivatives; Oxygen heterocycle; Tetrahydrofurane; Indium bromide; Chemical reduction; Carboxylic acid; Six membered ring; Dicarboxylic acid; Chemical synthesis
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201200727

An efficient reduction followed by cyclization of diacid compounds with the InBr3/TMDS system is reported. This system allows the formation of five‐ and six‐membered ring ethers substituted in the 3‐ or 4‐position. The efficient preparation of THF and THP derivatives from dicarboxylic acids is described. The reducing system used is InBr3/TMDS. Oxygenated rings were isolated in 17 to 98 % yield.