Ring opening of N-hydroxyphthalimide to construct phenylurea derivatives

被引：0

作者：

Wu, Yinhui ^{[1
]}

Lv, Bin ^{[1
]}

Zhang, Yanan ^{[1
]}

Gao, Pan ^{[1
]}

Zhang, Min ^{[2
]}

Yuan, Yu ^{[1
]}

机构：

[1] Yangzhou Univ, Sch Chem & Chem Engn, Yangzhou 225009, Jiangsu, Peoples R China

[2] Yangzhou Univ, Affiliated Hosp, Yangzhou 225009, Jiangsu, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2021年 / 51卷 / 13期

关键词：

N-hydroxyphthalimide; phenylurea; ring-opening reaction; construction of C– N bond; RUTHENIUM-CATALYZED PROTODECARBONYLATION; HOFMANN-TYPE REARRANGEMENT; PHTHALIMIDES; ACIDS;

D O I：

10.1080/00397911.2021.1919709

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Arylurea and their analogues have been one of the most ubiquitous backbone during the past century, and extensive studies have been conducted to establish practical synthetic methods for their derivatives. In particular, it is an effective pathway to synthesize arylureas by using commercially available phthalimide compounds. Reported herein is a triethoxyphosphine promoted ring-opening of the N-hydroxyphthalimide (NHPI) by the nucleophilic attack of amines. This transformation shows a wide range of functional-group tolerance under mild reaction conditions.

引用

页码：2025 / 2033

页数：9

共 26 条

[1]

Bruce, 2012, MACROMOLECULES, V45, P8155, DOI [10.1021/ma301639m, DOI 10.1021/MA301639M]

[2] Base-controlled product switch in the ruthenium-catalyzed protodecarbonylation of phthalimides: a mechanistic study [J].

D'Alterio, Massimo Christian ;

Yuan, Yu-Chao ;

Bruneau, Christian ;

Talarico, Giovanni ;

Gramage-Doria, Rafael ;

Poater, Albert .

CATALYSIS SCIENCE & TECHNOLOGY, 2020, 10 (01) :180-186

[3] Three-dimensional quantitative structure-activity relationship study on cyclic urea derivatives as HIV-1 protease inhibitors: Application of comparative molecular field analysis [J].

Debnath, AK .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (02) :249-259

[4] Discovery Process and Pharmacological Characterization of 2-(S)-(4-Fluoro-2-methylphenyl)piperazine-1-carboxylic Acid [1-(R)-(3,5-Bis-trifluoromethylphenyl)ethyl]methylamide (Vestipitant) as a Potent, Selective, and Orally Active NK1 Receptor Antagonist [J].

Di Fabio, Romano ;

Griffante, Cristiana ;

Alvaro, Giuseppe ;

Pentassuglia, Giorgio ;

Pizzi, Domenica A. ;

Donati, Daniele ;

Rossi, Tino ;

Guercio, Giuseppe ;

Mattioli, Mario ;

Cimarosti, Zadeo ;

Marchioro, Carla ;

Provera, Stefano ;

Zonzini, Laura ;

Montanari, Dino ;

Melotto, Sergio ;

Gerrard, Philip A. ;

Trist, David G. ;

Ratti, Emiliangeto ;

Corsi, Mauro .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (10) :3238-3247

[5]

Emmanuel, 2013, C RCHIM, V16, P350, DOI [10.1016/j.crci.2013.03.001, DOI 10.1016/J.CRCI.2013.03.001]

[6] NITRILE OXIDES .14. AN INVESTIGATION OF NITRILE OXIDE-ISOCYANATE REARRANGEMENT [J].

GRUNDMAN.C ;

KOCHS, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1970, 9 (08) :635-&

[7] One-pot reactions of N-(mesyloxy)phthalimides with secondary amines to 2-ureidobenzamides, 2-ureidobenzoic acids, ethyl 2-ureidobenzoates, or isatoic anhydrides [J].

Gütschow, M .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (14) :5109-5115

[8] Nickel-Mediated Decarbonylative Cross-Coupling of Phthalimides with in Situ Generated Diorganozinc Reagents [J].

Havlik, Sarah E. ;

Simmons, Jessica M. ;

Winton, Valerie J. ;

Johnson, Jeffrey B. .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (09) :3588-3593

[9]

ICHIKAWA Y, 1994, SYNLETT, P919

[10] Nickel-catalyzed decarbonylative addition of phthalimides to alkynes [J].

Kajita, Yuichi ;

Matsubara, Seijiro ;

Kurahashi, Takuya .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (19) :6058-+

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