Hypervalent Iodine(III)‐Mediated Benzannulation of Enamines with Alkynes: an Efficient Synthesis of Substituted Aminonaphthoic Acid Derivatives. Issue 4 (9th March 2015)

• Record Type: Journal Article
• Authors: Gao, Peng; Fan, Mingjin; Bai, Zijing; Wei, Yunyang
• Is Part Of: Chinese journal of chemistry. Volume 33:Issue 4(2015:Apr.)
• Page Start: 479
• Page End: 485
• Publication Date: 2015-03-09
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.201400802
• Languages: English
• ISSNs: 1001-604X

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p> An intermolecular two CC bond formation procedure for the synthesis of carbocycles mediated by hypervalent iodine(III) reagents was developed. This metal free protocol provided a new approach for the synthesis of useful substituted 1‐amino‐2‐naphthoic acid derivatives via benzannulation reactions. Various <italic>N</italic>‐unsubstituted and <italic>N</italic>‐alkyl substituted aromatic enamines with terminal alkynes and non‐terminal alkynes can be converted into corresponding 1‐amino‐2‐naphthoic acid derivatives under mild reaction conditions. When meta‐substituted phenyl enamines were employed in the reaction, two cyclization paths were detected in the reaction and <italic>ortho</italic>‐cyclization products were the only or major products. Good functional group tolerance, readily available material and high atom utilization efficiency make this method a potential procedure which may find broad application in organic synthesis.</p> </abstract>