One-Pot Synthesis of Ureas from Boc-Protected Amines

被引：70

作者：

Spyropoulos, Constantinos ^{[1
]}

Kokotos, Christoforos G. ^{[1
]}

机构：

[1] Univ Athens, Dept Chem, Organ Chem Lab, Athens 15771, Greece

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 10期

关键词：

SOLID-PHASE SYNTHESES; UNSYMMETRICAL UREAS; FACILE SYNTHESIS; EFFICIENT; DERIVATIVES; ACID; CARBONYLATION; CONVERSION; THIOUREAS; CLEAVAGE;

D O I：

10.1021/jo500492x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical one-pot synthesis of ureas is described. Boc-protected amines can be transformed into nonsymmetrical and symmetrical disubstituted and trisubstituted ureas utilizing 2-chloropyridine and trifluoromethanesulfonyl anhydride for the in situ generation of an isocyanate, which reacts with an amine. A variety of amines can be employed successfully, leading to high yields of isolated ureas.

引用

页码：4477 / 4483

页数：7

共 78 条

[1]

ADAMIAK RW, 1977, TETRAHEDRON LETT, P1935

[2] Synthesis and pyrolytic behaviour of thiazolidin-2-one 1,1-dioxides [J].

Aitken, RA ;

Armstrong, DP ;

Galt, RHB ;

Mesher, STE .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (14) :2139-2145

[3] Conversion of carbonimidodithioates into unsymmetrical di- and tri-substituted ureas including urea dipeptides [J].

Anbazhagan, M ;

Deshmukh, ARAS ;

Rajappa, S .

TETRAHEDRON LETTERS, 1998, 39 (21) :3609-3612

[4] Enzymatic removal of carboxyl protecting groups. 2. Cleavage of the benzyl and methyl moieties [J].

Barbayianni, E ;

Fotakopoulou, I ;

Schmidt, M ;

Constantinou-Kokotou, V ;

Bornscheuer, UT ;

Kokotos, G .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (22) :8730-8733

[5] SYNTHESIS OF N,N'-DISUBSTITUTED UREAS FROM CARBAMATES [J].

BASHA, A .

TETRAHEDRON LETTERS, 1988, 29 (21) :2525-2526

[6] An efficient new protocol for the formation of unsymmetrical tri- and tetrasubstituted ureas [J].

Batey, RA ;

Santhakumar, V ;

Yoshina-Ishii, C ;

Taylor, SD .

TETRAHEDRON LETTERS, 1998, 39 (35) :6267-6270

[7] A facile synthesis of unsymmetrical ureas [J].

Bogolubsky, Andrey V. ;

Ryabukhin, Sergey V. ;

Pipko, Sergey E. ;

Lukin, Oleg ;

Shivanyuk, Alexander ;

Mykytenko, Dmytro ;

Tolmachev, Andrey .

TETRAHEDRON, 2011, 67 (20) :3619-3623

[8] SOLID-PHASE SYNTHESES OF UNNATURAL BIOPOLYMERS CONTAINING REPEATING UREA UNITS [J].

BURGESS, K ;

LINTHICUM, DS ;

SHIN, HW .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (08) :907-909

[9] Solid phase syntheses of oligoureas [J].

Burgess, K ;

Ibarzo, J ;

Linthicum, DS ;

Russell, DH ;

Shin, H ;

Shitangkoon, A ;

Totani, R ;

Zhang, AJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (07) :1556-1564

[10] Asymmetric hydrogenation of unsaturated ureas with the BIPI ligands [J].

Busacca, Carl A. ;

Lorenz, Jon C. ;

Grinberg, Nelu ;

Haddad, Nizar ;

Lee, Heewon ;

Liang, Zhibin Li Mary ;

Reeves, Diana ;

Saha, Anjan ;

Varsolona, Rich ;

Senanayake, Chris H. .

ORGANIC LETTERS, 2008, 10 (02) :341-344

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