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.
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页码：9072 / 9076
页数：5
相关论文
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
    Aharonovich, Sinai
    Botoshansky, Mark
    Waymouth, Robert M.
    Eisen, Moris S.
    [J]. INORGANIC CHEMISTRY, 2010, 49 (20) : 9217 - 9229
  • [2] The action of organo-alkali compounds on benzonitrile
    Anker, RM
    Cook, AH
    [J]. 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
    ARMSTRONG, DR
    HENDERSON, KW
    MACGREGOR, M
    MULVEY, RE
    ROSS, MJ
    CLEGG, W
    ONEIL, PA
    [J]. 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
    ARMSTRONG, DR
    CLEGG, W
    MACGREGOR, M
    MULVEY, RE
    ONEIL, PA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (07) : 608 - 610
  • [6] Transition Metal Catalyzed Cycloisomerizations of 1,n-Allenynes and -Allenenes
    Aubert, Corinne
    Fensterbank, Louis
    Garcia, Pierre
    Malacria, Max
    Simonneau, Antoine
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1954 - 1993
  • [7] Formulation and in vitro assessment of minoxidil niosomes for enhanced skin delivery
    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
    [J]. 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
    Barluenga, Jose
    Fernandez-Rodriguez, Manuel Angel
    Garcia-Garcia, Patricia
    Aguilar, Enrique
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (09) : 2764 - +
  • [9] Synthesis of macrocycles via cobalt-mediated [2+2+2] cycloadditions
    Boñaga, LVR
    Zhang, HC
    Moretto, AF
    Ye, H
    Gauthier, DA
    Li, J
    Leo, GC
    Maryanoff, BE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (10) : 3473 - 3485
  • [10] HIGHLY REACTIVE MAGNESIUM AND ITS APPLICATION TO ORGANIC SYNTHESES
    BURNS, TP
    RIEKE, RD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (16) : 3674 - 3680
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