A novel approach to substituted 2H-azirines

被引：24

作者：

Katritzky, AR ^{[1
]}

Wang, MY ^{[1
]}

Wilkerson, CR ^{[1
]}

Yang, HF ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Ctr heterocycl Cpds, Gainesville, FL 32611 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 23期

关键词：

D O I：

10.1021/jo034472i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(Benzotriazol-1-yl)-2H-azirines 4a-c, obtained by treatment of oximes 2a-c with tosyl chloride and aqueous KOH, were reacted with benzylmagnesium bromide or 4-methylbenzylmagnesium bromide in the presence of zinc chloride to give 2-benzyl-2H-azirines 5a-f. Potassium phthalimide and sodium salt of benzenethiol converted 2-(benzotriazol-1-yl)-2H-azirines 4a-c into novel 2H-azirines 6a-c and 7 in good yields.

引用

页码：9105 / 9108

页数：4

共 26 条

[1] Reactions of methyl 2-aryl-2H-azirine-3-carboxylates with nucleophiles [J].

Alves, MJ ;

Gilchrist, TL ;

Sousa, JH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (10) :1305-1310

[2]

Banert K, 2000, EUR J ORG CHEM, V2000, P257

[3]

Gilchrist TL, 2000, SYNLETT, P1843

[4] BIOLOGICAL-ACTIVITY OF AMINOPHOSPHONIC ACIDS [J].

KAFARSKI, P ;

LEJCZAK, B .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1991, 63 (1-2) :193-215

[5] BtCH2TMS-assisted homologation of carboxylic acids:: A safe alternative to the Arndt-Eistert reaction [J].

Katritzky, AR ;

Zhang, SM ;

Fang, YF .

ORGANIC LETTERS, 2000, 2 (24) :3789-3791

[6] Properties and synthetic utility of N-substituted benzotriazoles [J].

Katritzky, AR ;

Lan, XF ;

Yang, JZ ;

Denisko, OV .

CHEMICAL REVIEWS, 1998, 98 (02) :409-548

[7] NOVEL CONVERSIONS OF BENZOTRIAZOL-1-YLMETHYL DERIVATIVES [J].

KATRITZKY, AR ;

WU, J ;

WROBEL, L ;

RACHWAL, S ;

STEEL, PJ .

ACTA CHEMICA SCANDINAVICA, 1993, 47 (02) :167-175

[8]

KATRITZKY AR, 1994, SYNTHESIS-STUTTGART, P597

[9] Reactivity of 2-halo-2H-azirines.: 1.: Reactions with nucleophiles [J].

Melo, TMVDPE ;

Lopes, CSJ ;

Gonsalves, AMDR ;

Beja, AM ;

Paixao, JA ;

Silva, MR ;

da Veiga, LA .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01) :66-71

[10]

Melo TMVDPE, 2000, TETRAHEDRON LETT, V41, P7217

← 1 2 3 →