An efficient one-pot synthesis of N,N′-disubstituted phenylureas and N-aryl carbamates using hydroxylamine-O-sulfonic acid

被引：8

作者：

Bao, Jennifer ^{[1
]}

Kuik, Dale ^{[1
]}

Tranmer, Geoffrey K. ^{[1
,2
]}

机构：

[1] Univ Manitoba, Fac Hlth Sci, Coll Pharm, Winnipeg, MB R3E 0T5, Canada

[2] Univ Manitoba, Fac Sci, Dept Chem, Winnipeg, MB R3T 2N2, Canada

来源：

TETRAHEDRON | 2018年 / 74卷 / 38期

基金：

加拿大自然科学与工程研究理事会;

关键词：

N; N '-disubstituted ureas; N-aryl carbamates; Hydroxylamine-O-sulfonic acid; Microwave-assisted organic synthesis; Lossen rearrangement; UREA DERIVATIVES; BIOLOGICAL EVALUATION; LOSSEN REARRANGEMENT; DISUBSTITUTED UREA; KINASE INHIBITORS; SUBSTITUTED UREAS; CARBOXYLIC-ACIDS; MILD CONDITIONS; DISCOVERY; ANILINES;

D O I：

10.1016/j.tet.2018.05.072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed an efficient one-pot method for the microwave-assisted synthesis of ureas and carbamates via a proposed Lossen rearrangement. Herein we report the first examples of the direct conversion of benzoyl chlorides into N,N'-disubstituted ureas and N-aryl carbamates using hydroxylamine-O-sulfonic acid as reagent. Using our general method, we have produced 11 examples of N,N'-disubstituted phenylureas in yields up to 95% using various substituted anilines, and primary and secondary amines. Additionally, we were able to generate a series of N-aryl carbamates in moderate yields using primary, secondary and tertiary alcohols. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：5546 / 5553

页数：8

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