通过Passerini/Staudinger/氮杂维蒂希/加成/亲核取代序列高效合成多取代3,4-二氢喹唑啉和4-3,1-苯并噻嗪。
New efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4-3,1-benzothiazines through a Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution sequence.
作者信息
Zhao Long, Yang Mao-Lin, Liu Min, Ding Ming-Wu
机构信息
Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Central China Normal University, Wuhan, 430079, P. R. China.
出版信息
Beilstein J Org Chem. 2022 Mar 4;18:286-292. doi: 10.3762/bjoc.18.32. eCollection 2022.
A new efficient synthesis of polysubstituted 3,4-dihydroquinazolines and 4-3,1-benzothiazines via sequential Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution reaction has been developed. The three-component Passerini reactions of 2-azidobenzaldehydes , benzoic acid (), and isocyanides produced the azide intermediates , which were treated sequentially with triphenylphosphine, isocyanates (or CS), and secondary amines to give polysubstituted 3,4-dihydroquinazolines and 4-3,1-benzothiazines in good overall yields through consecutive Passerini/Staudinger/aza-Wittig/addition/nucleophilic substitution reactions.
通过连续的Passerini/Staudinger/氮杂Wittig/加成/亲核取代反应，开发了一种新的高效合成多取代3,4-二氢喹唑啉和4,3,1-苯并噻嗪的方法。2-叠氮基苯甲醛、苯甲酸（）和异腈的三组分Passerini反应生成叠氮中间体，该中间体依次用三苯基膦、异氰酸酯（或CS₂）和仲胺处理，通过连续的Passerini/Staudinger/氮杂Wittig/加成/亲核取代反应，以良好的总收率得到多取代3,4-二氢喹唑啉和4,3,1-苯并噻嗪。
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