Microwave-induced one-pot synthesis of 4-ethynylbenzenesulfonamide

Chinese Journal of Applied Chemistry ›› 2009, Vol. 26 ›› Issue (09): 1120-1122.

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Microwave-induced one-pot synthesis of 4-ethynylbenzenesulfonamide

ZHANG Wen-Sheng1,2,KUANG Chun-Xiang1*

(1.Department of Chemistry,Tongji University,Shanghai 200092;
2.Department of Chemistry,Jiaozuo Teachers′ College,Jiaozuo)

Received:2008-09-04 Revised:2008-10-30 Published:2009-09-10 Online:2009-09-10

Abstract

Abstract:

One-pot simultaneous debrominative decarboxylation and sulfamation of anti-3-(4-chlorosulfonyl-benzyl)-2, 3-dibromopropanoic acid in DMF using aqueous ammonia (2.2 eq) under microwave irradiation condition for 25s stereoselectively afforded intermediate (Z)-4-(2-brompvinyl)benzenesulfonamides. The intermediates, without isolation and purification, were treated with 1,8-diazabicyclo[5.4.0]undec-7-ene ( DBU, 2 eq) under microwave irradiation condition for 1 min to give the desired 4-ethynylbenzenesulfonamide in a yield of 70%. The structure of the product was identified by 1H NMR, 13CNMR and IR.

Key words: sulfonamide, ethynylbenzene, one-pot, microwave irradiation

CLC Number:

O621.3

ZHANG Wen-Sheng1,2,KUANG Chun-Xiang1*. Microwave-induced one-pot synthesis of 4-ethynylbenzenesulfonamide[J]. Chinese Journal of Applied Chemistry, 2009, 26(09): 1120-1122.

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Microwave-induced one-pot synthesis of 4-ethynylbenzenesulfonamide

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