Yi-Long Zhu1, Bo Jiang2, Wen-Juan Hao3, Ai-Fang Wang3, Jiang-Kai Qiu1, Ping Wei4, De-Cai Wang4, Guigen Li5, Shu-Jiang Tu3. 1. School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China. laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn and Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing, 210009, Jiangsu, P. R. China. weiping@njtech.edu.cn. 2. School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China. laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn and Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA. 3. School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou 221116, P. R. China. laotu@jsnu.edu.cn jiangchem@jsnu.edu.cn. 4. Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing, 210009, Jiangsu, P. R. China. weiping@njtech.edu.cn. 5. Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA and Institute of Chemistry & Biomedical Sciences, Collaborative Innovation Center of Chemistry for Life Sciences, Nanjing University, Nanjing 210093, P. R. China.
Abstract
A new cascade three-component halosulfonylation of 1,7-enynes for efficient synthesis of densely functionalized 3,4-dihydroquinolin-2(1H)-ones has been established from readily accessible arylsulfonyl hydrazides and NIS (or NBS). The reaction pathway involves in situ-generated sulfonyl radical-triggered α,β-conjugated addition/6-exo-dig cyclization/radical coupling sequence, resulting in continuous multiple bond-forming events including C-S, C-C and C-I (or C-Br) bonds to rapidly build up molecular complexity.
A new cascade three-component halosulfonylation of n class="Chemical">1,7-enynes for efficient synthesis of densely functionalized 3,4-dihydroquinolin-2(1H)-ones has been established from readily accessible arylsulfonyl hydrazides and NIS (or NBS). The reaction pathway involves in situ-generated sulfonyl radical-triggered α,β-conjugated addition/6-exo-dig cyclization/radical coupling sequence, resulting in continuous multiple bond-forming events including C-S, C-C and C-I (or C-Br) bonds to rapidly build up molecular complexity.
Authors: N Neamati; A Mazumder; H Zhao; S Sunder; T R Burke; R J Schultz; Y Pommier Journal: Antimicrob Agents Chemother Date: 1997-02 Impact factor: 5.191