RHODIUM-CATALYZED [2+2+2] CYCLOADDITION FOR THE SYNTHESIS OF SUBSTITUTED PYRIDINES, PYRIDONES, AND THIOPYRANIMINES

被引:103
作者
Tanaka, Ken [1 ]
机构
[1] Tokyo Univ Agr & Technol, Grad Sch Engn, Dept Appl Chem, Koganei, Tokyo 1848588, Japan
关键词
2+2+2] Cycloaddition; Pyridine; Pyridone; Rhodium; Thiopyranimine; ONE-STEP SYNTHESIS; REGIOSELECTIVE INTERMOLECULAR CYCLOTRIMERIZATION; CATIONIC RHODIUM(I)/MODIFIED BINAP; TRANSITION-METAL-COMPLEXES; 2 DIFFERENT ALKYNES; ENANTIOSELECTIVE SYNTHESIS; 2,2'-BIPYRIDINE LIGANDS; UNACTIVATED NITRILES; SELECTIVE SYNTHESIS; AROMATIC-COMPOUNDS;
D O I
10.3987/REV-12-729
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The transition-metal-catalyzed [2+2+2] cycloaddition of alkynes with nitriles is a useful and atom-economical method for the synthesis of substituted pyridines. The use of isocyanates and isothiocyanates in place of nitriles affords substituted pyridones and thiopyranimines, respectively. This review comprehensively covers the [2+2+2] cycloaddition reactions catalyzed by rhodium complexes for the synthesis of substituted pyridines, pyridones, and thiopyranimines. Asymmetric variants of these rhodium-catalyzed [2+2+2] cycloaddition reactions are also described.
引用
收藏
页码:1017 / 1043
页数:27
相关论文
共 109 条
[41]   gem-Disubstituent effect:: Theoretical basis and synthetic applications [J].
Jung, ME ;
Piizzi, G .
CHEMICAL REVIEWS, 2005, 105 (05) :1735-1766
[42]   On-demand generation of an efficient catalyst for pyridine formation from unactivated nitriles and α,ω-diynes using CoCl2-6H2O, dppe, and Zn [J].
Kase, Kouki ;
Goswami, Avijit ;
Ohtaki, Kazuhiko ;
Tanabe, Emi ;
Saino, Naoko ;
Okamoto, Sentaro .
ORGANIC LETTERS, 2007, 9 (05) :931-934
[43]   Rhodium-Catalyzed Complete Regioselective Intermolecular Cross-Cyclotrimerization of Aryl Ethynyl Ethers and Nitriles or Isocyanates at Room Temperature [J].
Komine, Yoshiyuki ;
Tanaka, Ken .
ORGANIC LETTERS, 2010, 12 (06) :1312-1315
[44]   Flexible Synthesis of Fused Benzofuran Derivatives by Rhodium-Catalyzed [2+2+2] Cycloaddition with Phenol-Linked 1,6-Diynes [J].
Komine, Yoshiyuki ;
Kamisawa, Akiyoshi ;
Tanaka, Ken .
ORGANIC LETTERS, 2009, 11 (11) :2361-2364
[45]   Selective synthesis of 2-pyridones and pyrimidine-2,4-diones by neutral rhodium(I) complex-catalyzed cyclocotrimerization of alkynes and isocyanates [J].
Kondo, Teruyuki ;
Nomura, Masato ;
Ura, Yasuyuki ;
Wada, Kenji ;
Mitsudo, Take-aki .
TETRAHEDRON LETTERS, 2006, 47 (39) :7107-7111
[46]   A Serendipitous Discovery: Nickel Catalyst for the Cycloaddition of Diynes with Unactivated Nitriles [J].
Kumar, Puneet ;
Prescher, Simon ;
Louie, Janis .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (45) :10694-10698
[47]   Recent Development for Enantioselective Synthesis of Aromatic Compounds from Alkynes via Metallacyclopentadienes [J].
Li, Shi ;
Zhou, Lishan ;
Kanno, Ken-Ichiro ;
Takahashi, Tamotsu .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 48 (03) :517-528
[48]   Haloamidation of alkynes and related reactions using zirconacycles and isocyanates [J].
Li, YZ ;
Matsumura, H ;
Yamanaka, M ;
Takahashi, T .
TETRAHEDRON, 2004, 60 (06) :1393-1400
[49]   Pyridine-containing macrocycles via cobalt-mediated [2+2+2] cycloadditions of α,ω-bis-alkynes [J].
Maryanoff, Bruce E. ;
Zhang, Han-Cheng .
ARKIVOC, 2007, :7-35
[50]   A nickel-catalyzed route to pyridines [J].
McCormick, MM ;
Duong, HA ;
Zuo, G ;
Louie, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (14) :5030-5031