Regiocontrolled Gold-Catalyzed [2+2+2] Cycloadditions of Ynamides with Two Discrete Nitriles to Construct 4-Aminopyrimidine Cores

被引：129

作者：

Karad, Somnath Narayan ^{[1
]}

Liu, Rai-Shung ^{[1
]}

机构：

[1] Natl Tsing Hua Univ, Dept Chem, Hsinchu 30013, Taiwan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 34期

关键词：

cycloadditions; gold; heterocycles; homogeneous catalysis; synthetic methods; INDUCED CYCLOTRIMERIZATION REACTIONS; ENANTIOSELECTIVE SYNTHESIS; PYRIMIDINE-DERIVATIVES; TITANIUM(II) ALKOXIDE; UNACTIVATED NITRILES; PYRIDINE-DERIVATIVES; METALATED PYRIDINES; ORGANIC NITRILES; ROOM-TEMPERATURE; ALKYNES;

D O I：

10.1002/anie.201405312

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reported herein is the novel gold-catalyzed intermolecular [2+2+2] cycloaddition of ynamides with two discrete nitriles to form monomeric 4-aminopyrimidines, which are pharmaceutically important structural motifs. The utility of this new cycloaddition is demonstrated by the excellent regioselectivity obtained using a variety of ynamides and nitriles.

引用

页码：9072 / 9076

页数：5

共 88 条

[1] Chemoselectivity Diversity in the Reaction of LiNC6F5SiMe3 with Nitriles and the Synthesis, Structure, and Reactivity of Zirconium Mono- and Tris[2-(2-pyridyl)tetrafluorobenzimidazolate] Complexes [J].

Aharonovich, Sinai ;

Botoshansky, Mark ;

Waymouth, Robert M. ;

Eisen, Moris S. .

INORGANIC CHEMISTRY, 2010, 49 (20) :9217-9229

[2] The action of organo-alkali compounds on benzonitrile [J].

Anker, RM ;

Cook, AH .

JOURNAL OF THE CHEMICAL SOCIETY, 1941, :323-331

[3]

[Anonymous], 2011, ANGEW CHEM-GER EDI

[4] SYNTHETIC AND THEORETICAL MO CALCULATIONAL STUDIES OF LITHIOTRIAZINE INTERMEDIATES PRODUCED DURING ALKYLLITHIUM-INDUCED CYCLOTRIMERIZATION REACTIONS OF ORGANIC NITRILES, AND COMPARISON OF THEIR STRUCTURES WITH THAT OF A METHYLMAGNESIOTRIAZINE DERIVATIVE [J].

ARMSTRONG, DR ;

HENDERSON, KW ;

MACGREGOR, M ;

MULVEY, RE ;

ROSS, MJ ;

CLEGG, W ;

ONEIL, PA .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1995, 486 (1-2) :79-93

[5] BUTYLLITHIUM-INDUCED CYCLOTRIMERIZATION REACTIONS OF ORGANIC NITRILES - SOLVENT DEPENDENCY, CRYSTAL AND SOLUTION STRUCTURES OF LITHIO TRIAZINE INTERMEDIATES AND AN UNEXPECTED REARRANGEMENT OF DIHYDROTRIAZINO ANIONS [J].

ARMSTRONG, DR ;

CLEGG, W ;

MACGREGOR, M ;

MULVEY, RE ;

ONEIL, PA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (07) :608-610

[6] Transition Metal Catalyzed Cycloisomerizations of 1,n-Allenynes and -Allenenes [J].

Aubert, Corinne ;

Fensterbank, Louis ;

Garcia, Pierre ;

Malacria, Max ;

Simonneau, Antoine .

CHEMICAL REVIEWS, 2011, 111 (03) :1954-1993

[7] Formulation and in vitro assessment of minoxidil niosomes for enhanced skin delivery [J].

Balakrishnana, Prabagar ;

Shanmugam, Srinivasan ;

Lee, Won Seok ;

Lee, Won Mo ;

Kim, Jong Oh ;

Oh, Dong Hoon ;

Kim, Dae-Duk ;

Kim, Jung Sun ;

Yoo, Bong Kyu ;

Choi, Han-Gon ;

Woo, Jong Soo ;

Yong, Chul Soon .

INTERNATIONAL JOURNAL OF PHARMACEUTICS, 2009, 377 (1-2) :1-8

[8] Gold-catalyzed intermolecular Hetero-Dehydro-Diels-Alder cycloaddition of captodative dienynes with nitriles:: A new reaction and regioselective direct access to pyridines [J].

Barluenga, Jose ;

Fernandez-Rodriguez, Manuel Angel ;

Garcia-Garcia, Patricia ;

Aguilar, Enrique .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (09) :2764-+

[9] 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

[10] HIGHLY REACTIVE MAGNESIUM AND ITS APPLICATION TO ORGANIC SYNTHESES [J].

BURNS, TP ;

RIEKE, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (16) :3674-3680

← 1 2 3 4 5 6 7 8 9 →