TfOH-mediated [2+2+2] cycloadditions of ynamides with two discrete nitriles: synthesis of 4-aminopyrimidine derivatives

被引：36

作者：

Chen, Ping ^{[1
]}

Song, Cai-xia ^{[1
]}

Wang, Wan-shu ^{[1
]}

Yu, Xue-liang ^{[1
]}

Tang, Yu ^{[1
,2
]}

机构：

[1] Tianjin Univ, Sch Pharmaceut Sci & Technol, Key Lab Modern Drug Delivery & High Efficiency, Tianjin 300072, Peoples R China

[2] Ocean Univ China, Key Lab Marine Drugs, Chinese Minist Educ, Sch Med & Pharm, 5 Yushan Rd, Qingdao, Peoples R China

来源：

RSC ADVANCES | 2016年 / 6卷 / 83期

基金：

中国国家自然科学基金;

关键词：

ONE-STEP SYNTHESIS; CYCLIZATION; CASCADES;

D O I：

10.1039/c6ra11408c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this study, a concise and atom-economical TfOH-mediated [2 + 2 + 2] cycloaddition of ynamides with two discrete nitriles is developed to synthesize multi-substituted 4-aminopyrimidine. A variety of functional groups and sterically and electronically diverse reaction partners are tolerated. The products were obtained in good to excellent yields.

引用

页码：80055 / 80058

页数：4

共 45 条

[1] Radical cyclization of ynamides into six- or eight-membered rings. Application to the synthesis of a protoberberine analog [J].

Balieu, Sebastien ;

Toutah, Krimo ;

Carro, Laura ;

Chamoreau, Lise-Marie ;

Rousseliere, Helene ;

Courillon, Christine .

TETRAHEDRON LETTERS, 2011, 52 (22) :2876-2880

[2] Synthesis of macrocycles via cobalt-mediated [2+2+2] cycloadditions [J].

Boñaga, LVR ;

Zhang, HC ;

Moretto, AF ;

Ye, H ;

Gauthier, DA ;

Li, J ;

Leo, GC ;

Maryanoff, BE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) :3473-3485

[3] Synthesis of Functionalized Allenamides from Ynamides by Enolate Claisen Rearrangement [J].

Brioche, Julien ;

Meyer, Christophe ;

Cossy, Janine .

ORGANIC LETTERS, 2013, 15 (07) :1626-1629

[4]

Carcia P. G., 2009, CHEM-EUR J, V15, P2129

[5] 2,4,6-trisubstituted pyrimidines as a new class of selective adenosine A1 receptor antagonists [J].

Chang, LCW ;

Spanjersberg, RF ;

Künzel, JKV ;

Mulder-Krieger, T ;

van den Hout, G ;

Beukers, MW ;

Brussee, J ;

IJzerman, AP .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (26) :6529-6540

[6] Radical Zinc-Atom Transfer Based Multicomponent Approaches to 3-Alkylidene-Substituted Tetrahydrofurans [J].

Chemla, Fabrice ;

Dulong, Florian ;

Ferreira, Franck ;

Nuellen, Max P. ;

Perez-Luna, Alejandro .

SYNTHESIS-STUTTGART, 2011, (09) :1347-1360

[7] [2+2+2] Cycloadditions of Alkynylynamides - A Total Synthesis of Perlolyrine and the First Total Synthesis of "Isoperlolyrine" [J].

Dassonneville, Benjamin ;

Witulski, Bernhard ;

Detert, Heiner .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (15) :2836-2844

[8] Carbocyclization Cascades of Ally! Ketenimines via Aza-Claisen Rearrangements of N-Phosphoryl-N-allyl-ynamides [J].

DeKorver, Kyle A. ;

Wang, Xiao-Na ;

Walton, Mary C. ;

Hsung, Richard P. .

ORGANIC LETTERS, 2012, 14 (07) :1768-1771

[9] Ynamides: A Modern Functional Group for the New Millennium [J].

DeKorver, Kyle A. ;

Li, Hongyan ;

Lohse, Andrew G. ;

Hayashi, Ryuji ;

Lu, Zhenjie ;

Zhang, Yu ;

Hsung, Richard P. .

CHEMICAL REVIEWS, 2010, 110 (09) :5064-5106

[10] Ynamides: Versatile Tools in Organic Synthesis [J].

Evano, Gwilherm ;

Coste, Alexis ;

Jouvin, Kevin .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (16) :2840-2859

← 1 2 3 4 5 →