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

被引:25
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
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 53 条
[1]   In vitro and in vivo pharmacological profile of AS057278, a selective D-amino acid oxidase inhibitor with potential anti-psychotic properties [J].
Adage, Tiziana ;
Trillat, Anne-Cecile ;
Quattropani, Anna ;
Perrin, Dominique ;
Cavare, Laurent ;
Shaw, Jeffrey ;
Guerassimenko, Oxana ;
Giachetti, Claudio ;
Greco, Beatrice ;
Chumakov, Ilya ;
Halazy, Serge ;
Roach, Arthur ;
Zaratin, Paola .
EUROPEAN NEUROPSYCHOPHARMACOLOGY, 2008, 18 (03) :200-214
[2]  
Aggarwal VK, 2001, ANGEW CHEM INT EDIT, V40, P1430, DOI 10.1002/1521-3773(20010417)40:8<1430::AID-ANIE1430>3.0.CO
[3]  
2-W
[4]  
Arndt F., 1943, ORG SYNTH, V2, P461
[5]  
Bartels A, 1998, SYNTHESIS-STUTTGART, P1645
[6]   NEW MECHANISM FOR FORMATION OF CYCLOPROPANE DERIVATIVES IN THERMOLYSIS OF PYRAZOLINES [J].
BEGLEY, MJ ;
DEAN, FM ;
HOUGHTON, LE ;
JOHNSON, RS ;
PARK, BK .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (11) :461-462
[7]  
Creary X., 1990, ORG SYNTH, V7, P438
[8]  
de Boer T.J., 1963, ORG SYNTH, V4, P250
[9]   ASYMMETRIC 1,3-DIPOLAR CYCLO-ADDITIONS TO 5-MENTHYLOXY-2[5H]-FURANONES [J].
DELANGE, B ;
FERINGA, BL .
TETRAHEDRON LETTERS, 1988, 29 (41) :5317-5320
[10]  
Elguero J., 1996, COMPREHENSIVE HETERO, V3, P1, DOI DOI 10.1016/B978-008096518-5.00059-9