Synthesis of 2-Aminoquinazolinones via Carbonylative Coupling of ortho-lodoanilines and Cyanamide

被引：27

作者：

Akerbladh, Linda ^{[1
]}

Odell, Luke R. ^{[1
]}

机构：

[1] Uppsala Univ, Dept Med Chem, Organ Pharmaceut Chem, BMC, Box 574, SE-75123 Uppsala, Sweden

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 07期

关键词：

PALLADIUM-CATALYZED CYCLOCARBONYLATION; SOLID-PHASE SYNTHESIS; EX-SITU GENERATION; CARBON-MONOXIDE; MOLYBDENUM HEXACARBONYL; QUINAZOLIN-4(3H)-ONE MOIETY; ANTIINFLAMMATORY AGENTS; OXALYL CHLORIDE; AROMATIC-AMINES; O-IODOANILINES;

D O I：

10.1021/acs.joc.6b00249

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we describe a convenient and efficient synthesis of 2-aminoquinazolin-4(3H)-ones and N1-substituted 2-aminoquinazolin-4(1H)-ones by a domino carbonylation/cyclization process. The reaction proceeds via carbonylative coupling of readily available ortho-iodoanilines with cyanamide followed by in situ ring closure of an N-cyanobenzamide intermediate. The products were easily isolated by precipitation in moderate to excellent yields for a wide range of substrates, making this a highly attractive method for the synthesis of 2-aminoquinazolinones.

引用

页码：2966 / 2973

页数：8

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