1,3-Dipolar cycloadditions of 2-thio-3-chloroacrylamides with diazoalkanes

被引：24
|
作者：
Kissane, Marie [1 ]
Lawrence, Simon E. [1 ]
Maguire, Anita R. [1 ,2 ]
机构：
[1] Natl Univ Ireland Univ Coll Cork, Dept Chem, Analyt & Biol Chem Res Facil, Cork, Ireland
[2] Natl Univ Ireland Univ Coll Cork, Sch Pharm, Analyt & Biol Chem Res Facil, Cork, Ireland
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 12期
关键词：
THIO-BETA-CHLOROACRYLAMIDES; NIACIN RECEPTOR GPR109A; CHIRAL DIPOLAROPHILES; ALPHA-THIOAMIDES; NICOTINIC-ACID; IDENTIFICATION; SULFOXIDES; DIAZOMETHANE; TAUTOMERISM; THERMOLYSIS;
D O I：
10.1039/c002479a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Thio-3-chloroacrylamides undergo 1,3-dipolar cycloadditions with diazoalkanes leading to a series of novel pyrazolines and pyrazoles. The mechanistic and synthetic features of the cycloadditions to the 2-thio-3-chloroacrylamides at both the sulfide and sulfoxide levels of oxidation are rationalised on the basis of the nature of the substituents.
引用
收藏
页码：2735 / 2748
页数：14
相关论文
共 50 条
  • [31] Stereoselective intramolecular 1,3-dipolar cycloadditions
    Namboothiri, INN
    Hassner, A
    STEREOSELECTIVE HETEROCYCLIC SYNTHESIS III, 2001, 216 : 1 - 49
  • [32] CENTENARY LECTURE - 1,3-DIPOLAR CYCLOADDITIONS
    HUISGEN, R
    PROCEEDINGS OF THE CHEMICAL SOCIETY OF LONDON, 1961, (OCT): : 357 - &
  • [33] Understanding the 1,3-Dipolar Cycloadditions of Allenes
    Yu, Song
    Vermeeren, Pascal
    van Dommelen, Kevin
    Bickelhaupt, F. Matthias
    Hamlin, Trevor A.
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (50) : 11529 - 11539
  • [34] 1,3-DIPOLAR CYCLOADDITIONS OF FULMINIC ACID
    HUISGEN, R
    CHRISTL, M
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (05) : 456 - &
  • [35] 1,3-dipolar cycloadditions in aqueous media
    Molteni, Giorgio
    HETEROCYCLES, 2006, 68 (10) : 2177 - +
  • [36] REGIOSELECTIVITY AND REACTIVITY IN 1,3-DIPOLAR CYCLOADDITIONS OF DIAZONIUM BETAINES (DIAZOALKANES, AZIDES, AND NITROUS-OXIDE)
    HOUK, KN
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (25) : 8953 - &
  • [37] 1,3-DIPOLAR CYCLOADDITIONS OF DIAZOALKANES TO HETEROAROMATIC SYSTEMS - NEW SIMPLE SYNTHESES OF C-NUCLEOSIDES
    STANOVNIK, B
    JELEN, B
    ZLICAR, M
    FARMACO, 1993, 48 (02): : 231 - 242
  • [38] 1,3-dipolar cycloadditions of α-methoxycarbonylnitrones in the presence of Eu(fod)3
    Tamura, O
    Mita, N
    Gotanda, K
    Yamada, K
    Nakano, T
    Katagiri, R
    Sakamoto, M
    HETEROCYCLES, 1997, 46 : 95 - 99
  • [39] Carbonyl ylide 1,3-dipolar cycloadditions with porphyrins
    Flemming, J
    Dolphin, D
    TETRAHEDRON LETTERS, 2002, 43 (40) : 7281 - 7283
  • [40] Iridium-Catalyzed 1,3-Dipolar Cycloadditions
    Carmona, Daniel
    Oro, Luis A.
    IRIDIUM CATALYSIS, 2011, 34 : 209 - 229
12345