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

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

页码：2735 / 2748

页数：14

共 53 条

[11] MECHANISM OF THE THERMAL AND PHOTOCHEMICAL DECOMPOSITION OF AZOALKANES [J].

ENGEL, PS .

CHEMICAL REVIEWS, 1980, 80 (02) :99-150

[12]

Fleming I., 2007, Frontier orbitals and organic chemical reactions, P1

[13] Agonist lead identification for the high affinity niacin receptor GPR109a [J].

Gharbaoui, Tawfik ;

Skinner, Philip J. ;

Shin, Young-Jun ;

Averbuj, Claudia ;

Jung, Jae-Kyu ;

Johnson, Benjamin R. ;

Duong, Tracy ;

Decaire, Marc ;

Uy, Jane ;

Cherrier, Martin C. ;

Webb, Peter J. ;

Tamura, Susan Y. ;

Zou, Ning ;

Rodriguez, Nathalie ;

Boatman, P. Douglas ;

Sage, Carleton R. ;

Lindstrom, Andrew ;

Xu, Jerry ;

Schrader, Thomas O. ;

Smith, Brian M. ;

Chen, Ruoping ;

Richman, Jeremy G. ;

Connolly, Daniel T. ;

Colletti, Steven L. ;

Tata, James R. ;

Semple, Graeme .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (17) :4914-4919

[14]

Gilchrist T.L., 1979, Organic Reactions and Orbital Symmetry, VSecond

[15] STRUCTURE ACTIVITY RELATIONSHIPS IN A SERIES OF FUNGICIDAL PYRAZOLE CARBOXANILIDES [J].

HUPPATZ, JL ;

PHILLIPS, JN ;

WITRZENS, B .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1984, 48 (01) :45-50

[16] Substitution of hydroxybiaryls via directed ortho-lithiation of N-silylated O-aryl N-isopropylcarbamates [J].

Kauch, M ;

Snieckus, V ;

Hoppe, D .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (18) :7149-7158

[17] Investigation of the reaction of α-thioamides, α-esters and α-nitriles with N-halosuccinimides [J].

Kissane, Marie ;

Murphy, Maureen ;

Lynch, Denis ;

Ford, Alan ;

Maguire, Anita R. .

TETRAHEDRON, 2008, 64 (32) :7639-7649

[18] Investigation of the chemoselective and enantioselective oxidation of α-thio-β-chloroacrylamides [J].

Kissane, Marie ;

Lynch, Denis ;

Chopra, Jay ;

Lawrence, Simon E. ;

Maguire, Anita R. .

TETRAHEDRON-ASYMMETRY, 2008, 19 (10) :1256-1273

[19] Asymmetric 1,3-dipolar cycloadditions of acrylamides [J].

Kissane, Marie ;

Maguire, Anita R. .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (02) :845-883

[20] SYNTHESIS AND STEREOCHEMISTRY OF 5-SUBSTITUTED 2-METHYLCYCLOHEPTANONES [J].

MARSHALL, JA ;

PARTRIDGE, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (11) :4090-+

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