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

共 50 条

[21] Novel and efficient one-pot synthesis of N′-alkyl-N,N-dimethylacetamidines
Li, Zhe-Qi
Wang, Hui-Long
JOURNAL OF CHEMICAL RESEARCH, 2011, (02) : 119 - 120
[22] Expeditious one-pot three component synthesis of N-aryl dithiocarbamate derivatives using mesoporous Cu-materials
Payra, Soumen
Saha, Arijit
Peng, Rui
Wu, Chia-Ming
Koodali, Ranjit T.
Banerjee, Subhash
TETRAHEDRON LETTERS, 2015, 56 (13) : 1609 - 1613
[23] Succinimide-N-sulfonic acid Catalyzed One Pot, Efficient Synthesis of Substituted Pyrazoles
Kande, Sagar R.
ORIENTAL JOURNAL OF CHEMISTRY, 2022, 38 (04) : 1059 - 1063
[24] Synthesis of N-Aryl Carbamates from Aryl(TMP)iodonium Salts via C-N Coupling
Hatton, Joseph
Stuart, David R.
ORGANIC LETTERS, 2025,
[25] A convenient "one-pot" reaction for selective monoalkylation of N,N′-disubstituted ethylenediamines
Salerno, A
Figueroa, MA
Perillo, IA
SYNTHETIC COMMUNICATIONS, 2003, 33 (18) : 3193 - 3204
[26] Convenient one-pot synthesis of N-aryl-3-pyrrolines.
Venkatachalam, CS
Jayaprakash, K
Balasubramanian, KK
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U218 - U218
[27] A convenient one-pot synthesis of N-aryl-3-pyrrolines
Jayaprakash, K
Venkatachalam, CS
Balasubramanian, KK
TETRAHEDRON LETTERS, 1999, 40 (35) : 6493 - 6496
[28] Modification of the Tiemann rearrangement:: One-pot synthesis of N,N-disubstituted cyanamides from amidoximes
Bakunov, SA
Rukavishnikov, AV
Tkachev, AV
SYNTHESIS-STUTTGART, 2000, (08): : 1148 - 1159
[29] Microwave promoted solvent-free one-pot synthesis of N,N′-disubstituted urea derivatives
Jadhav, VH
Deshpande, SS
Borate, HB
Wakharkar, RD
JOURNAL OF CHEMICAL RESEARCH, 2005, (03) : 205 - 208
[30] One-pot synthesis of 2,3-disubstituted N-tosylindoles from o-acyl-N-tosylanilines
Hari, Y
Kanie, T
Miyagi, T
Aoyama, T
SYNTHESIS-STUTTGART, 2006, (08): : 1249 - 1252

← 1 2 3 4 5 →