REGIOSELECTIVE ACYLATIONS OF KETONES TO 1,3-DIKETONES VIA METALATED DIMETHYLHYDRAZONES

被引：13

作者：

ENDERS, D

PATHAK, VN

WEUSTER, P

机构：

[1] Institut für Organische Chemie, Technischen Hochschule Aachen, Aachen, W-5100

来源：

CHEMISCHE BERICHTE-RECUEIL | 1992年 / 125卷 / 02期

关键词：

DIMETHYLHYDRAZONES; METALATED; ACYLATION; REGIOSELECTIVE; 1,3-DIKETONES; ALPHA-CYANO DIMETHYLHYDRAZONES;

D O I：

10.1002/cber.19921250232

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Acyclic and cyclic unsymmetrical ketones 1 are regioselectively acylated via their corresponding metalated dimethylhydrazones 3 by using acid chlorides or anhydrides, arylnitriles, ethyl formate, carbon disulfide/methyl iodide, alkyl chloroformates, dialkyl carbonates, phenyl isocyanate, or phenyl isothiocyanate as acylating agents. Subsequent acidic hydrolysis leads to the 1,3-diketones 6 in acceptable to excellent overall yields. The tautomeric structure of the product hydrazones 4, 5, 7, and 8 is determined. Cyanation of 3 with cyanogen bromide affords the alpha-cyano dimethylhydrazones 9.

引用

页码：515 / 524

页数：10

共 72 条

[1]

ABRAMOVITCH RA, 1979, POL J CHEM, V53, P177

[2]

AGER JW, 1966, TETRAHEDRON S, V7, P277

[3]

ALHAJJAR FH, 1977, CHEM PHARM BULL, V25, P548

[4] REACTION OF ENAMINOSILANE - SELECTIVE C-ACYLATION OF ENAMINOSILANES WITH ACID-CHLORIDES [J].

ANDO, W ;

TSUMAKI, H .

TETRAHEDRON LETTERS, 1982, 23 (30) :3073-3076

[5]

BECK AK, 1977, TETRAHEDRON LETT, P1187

[6]

BRAM G, 1964, B SOC CHIM FR, P945

[7]

Brooks D. W., 1979, ANGEW CHEM, V91, P76

[8] C-ACYLATION UNDER VIRTUALLY NEUTRAL CONDITIONS [J].

BROOKS, DW ;

LU, LDL ;

MASAMUNE, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (01) :72-74

[9] SYNTHETIC ROUTES TO POLYFUNCTIONAL MOLECULES VIA METALLATED DIMETHYLHYDRAZONES [J].

COREY, EJ ;

ENDERS, D .

CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (04) :1362-1383

[10] GENERATION AND SYNTHETIC USE OF METALLATED DIMETHYLHYDRAZONES REGION AND STEREOSELECTIVE ALKYLATION OF CARBONYL-COMPOUNDS [J].

COREY, EJ ;

ENDERS, D .

CHEMISCHE BERICHTE-RECUEIL, 1978, 111 (04) :1337-1361

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