Copper(I)‐catalyzed Cyclization Reactions of Ethyl (E)‐α‐Ethynyl‐β‐Aryl‐α,β‐Unsaturated Esters with N‐Sulfonyl Azides: Synthesis of 1‐Aminonaphthalene, 3‐Aminobenzofuran, and 3‐Aminothiobenzofuran Derivatives

Autor:	Son, Jeong‐Yu, Han, Gi Uk, Ko, Gi Hoon, Maeng, Chanyoung, Shin, Seohyun, Lee, Phil Ho
Předmět:	COPPER AZIDES ESTERS SULFONYL compounds RING formation (Chemistry) NITROGEN
Zdroj:	Bulletin of the Korean Chemical Society; Jul2019, Vol. 40 Issue 7, p696-703, 8p
Abstrakt:	A synthetic method for ethyl 4‐(alkyl or arylsulfonamido)‐2‐naphthoates from ethyl (E)‐α‐ethynyl‐β‐aryl‐α,β‐unsaturated esters (1) and N‐sulfonyl azides (2) in the presence of 2,6‐lutidine in THF at 60 °C for 3 h was developed in one step, in which a copper(I)‐catalyzed 1,3‐dipolar cycloaddition, ketenimine formation, and 6π‐electrocyclization followed by [1,3]‐H shift tandem reaction took place. This method enabled efficient synthesis of a wide range of 1‐aminonaphthalene and 3‐aminobenzofuran and 3‐aminobenzothiophene derivatives with the release of molecular nitrogen. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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