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通过一锅三组分反应高效合成螺[色烯并[2,3 - d]嘧啶 - 5,3'-吲哚啉] - 四酮

Efficient synthesis of spiro[chromeno[2,3-d]pyrimidine-5,3'-indoline]-tetraones by a one-pot and three-component reaction.

作者信息

Jadidi Khosrow, Ghahremanzadeh Ramin, Bazgir Ayoob

机构信息

Department of Chemistry, Shahid Beheshti University, Tehran, Iran.

出版信息

J Comb Chem. 2009 May-Jun;11(3):341-4. doi: 10.1021/cc800167h.

DOI:10.1021/cc800167h
PMID:19239200
Abstract

An efficient one-pot synthesis of novel 8,9-dihydrospiro[chromeno[2,3-d]pyrimidine-5,3'-indoline]-2,2',4,6(1H,3H,7H)-tetraone derivatives by a three-component condensation reaction of barbituric acids, isatins and cyclohexane-1,3-diones in refluxing water in the presence of p-TSA for 10 h is reported. Two cyclohexane-1,3-diones, three barbituric acids, and eight substituted isatins were chosen for the library validation. Reaction of 5,5-dimethyl-cyclohexane-1,3-dione and acenaphthylene-1,2-dione with barbituric acids resulted in the formation of spiro[acenaphthylene-1,5'-chromeno[2,3-d]pyrimidine] derivatives.

摘要

报道了在对甲苯磺酸存在下,巴比妥酸、异吲哚酮和环己烷-1,3-二酮在回流水中进行三组分缩合反应,高效一锅法合成新型8,9-二氢螺[色烯并[2,3-d]嘧啶-5,3'-吲哚啉]-2,2',4,6(1H,3H,7H)-四酮衍生物,反应时间为10小时。选择了两种环己烷-1,3-二酮、三种巴比妥酸和八种取代异吲哚酮进行文库验证。5,5-二甲基-环己烷-1,3-二酮和苊烯-1,2-二酮与巴比妥酸反应生成螺[苊烯-1,5'-色烯并[2,3-d]嘧啶]衍生物。

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