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β-氧代二硫酯在多米诺反应和多组分反应中的应用:通往二氢嘧啶和香豆素的简便途径。

Application of beta-oxodithioesters in domino and multicomponent reactions: facile route to dihydropyrimidines and coumarins.

作者信息

Singh Okram Mukherjee, Devi Nepram Sushuma

机构信息

Department of Chemistry, Manipur University, Canchipur-795003, India.

出版信息

J Org Chem. 2009 Apr 17;74(8):3141-4. doi: 10.1021/jo802585b.

Abstract

A facile route to hitherto unknown 5-methylmercaptothiocarbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones and substituted 2H-chromene-2-thiones has been developed. SnCl(2)-catalyzed cyclocondensation of beta-oxodithioesters with a variety of readily accessible aldehydes and urea affords the dihydropyrimidinones. The methodology involves the three-component Biginelli reaction. On the other hand, substituted salicylaldehyde and beta-oxodithioesters reacted under the same condition to afford the substituted 2H-chromene-2-thiones in high yields.

摘要

已经开发出一种简便的方法来合成迄今未知的5-甲基巯基硫代羰基-4-芳基-3,4-二氢嘧啶-2(1H)-酮和取代的2H-色烯-2-硫酮。SnCl(2)催化β-氧代二硫酯与各种易于获得的醛和尿素进行环缩合反应,得到二氢嘧啶酮。该方法涉及三组分Biginelli反应。另一方面,取代的水杨醛和β-氧代二硫酯在相同条件下反应,以高产率得到取代的2H-色烯-2-硫酮。

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