Synthesis of Spiro[benzo[d][1,3]oxazine-4,4′-isoquinoline]s via [4+1+1] Annulation of N-Aryl Amidines with Diazo Homophthalimides and O2

被引：53

作者：

Zhou, Qianting ^{[1
]}

Song, Xia ^{[1
]}

Zhang, Xinying ^{[1
]}

Fan, Xuesen ^{[1
]}

机构：

[1] Henan Normal Univ, Sch Chem & Chem Engn, Minist Educ,Key Lab Green Chem Media & React, NMPA Key Lab Res & Evaluat Innovat Drugs,Collabor, Xinxiang 453007, Henan, Peoples R China

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 06期

基金：

中国国家自然科学基金;

关键词：

C-H FUNCTIONALIZATION; HIGHLY EFFICIENT; OLEFINIC AMIDES; DIVERGENT COUPLINGS; SELECTIVE SYNTHESIS; HYDROXYLATION; ACTIVATION; 2-ARYLINDOLES; ISOQUINOLINES; CYCLIZATION;

D O I：

10.1021/acs.orglett.1c04193

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Synthesis of spiro [benzo[d][1,3]oxazine-4,4 '- isoquinoline]s through a unique [4+1+1] annulation of N-aryl amidines with diazo homophthalimides and O-2 is presented. This unprecedented spirocyclization reaction features readily obtainable substrates, structurally and pharmaceutically attractive products, a cost-free and clean oxygen source, sustainable reaction medium, tolerance of a broad spectrum of functional groups, and an interesting reaction mechanism based on sequential C(sp(2))-H/ C(sp(3))-H bond cleavage and oxygen insertion.

引用

页码：1280 / 1285

页数：6

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