SYNTHESIS OF 2-CHLORO-4,6-DI(HETEROARYL)PYRIMIDINES

被引：33

作者：

STREKOWSKI, L

HARDEN, DB

GRUBB, WB

PATTERSON, SE

CZARNY, A

MOKROSZ, MJ

CEGLA, MT

WYDRA, RL

机构：

[1] Department of Chemistry, Georgia State University, Atlanta, Georgia

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1990年 / 27卷 / 05期

关键词：

D O I：

10.1002/jhet.5570270539

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A practical method for the preparation of 2‐chloro‐4,6‐di(heteroaryl)pyrimidines and their 5‐methyl homologues from readily available 2‐chloropyrimidine and 2‐chloro‐5‐methylpyrimidine, respectively, is described. The method is based on the addition reactions of heteroaryllithium reagents with chloropyrimidines followed by dehydrogenation of the resultant substituted dihydropyrimidines. The use of 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone as the dehydrogenation agent gives the best results. Side reactions in the addition step are discussed. Copyright © 1990 Journal of Heterocyclic Chemistry

引用

页码：1393 / 1400

页数：8

共 21 条

[1] FORMAMID-REAKTIONEN .11. DARSTELLUNG, EIGENSCHAFTEN UND UMSETZUNGEN DES PYRIMIDINS [J].

BREDERECK, H ;

GOMPPER, R ;

HERLINGER, H .

CHEMISCHE BERICHTE-RECUEIL, 1958, 91 (12) :2832-2849

[2] UNFUSED HETEROBICYCLES AS AMPLIFIERS OF PHLEOMYCIN .6. SOME THIENYL-PYRIMIDINES AND THIAZOLYL-PYRIMIDINES WITH STRONGLY BASIC SIDE-CHAINS [J].

BROWN, DJ ;

COWDEN, WB ;

STREKOWSKI, L .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1982, 35 (06) :1209-1214

[3] ISOMERIZATIONS AKIN TO DIMROTH REARRANGEMENT .3. CONVERSION OF SIMPLE S-TRIAZOLO[4,3-A]PYRIMIDINES INTO THEIR [1,5-A] ISOMERS [J].

BROWN, DJ ;

NAGAMATSU, T .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1977, 30 (11) :2515-2525

[4]

BROWN DJ, 1985, PYRIMIDINES S, V2, P180

[5] NICKEL-COMPLEX CATALYSIS IN THE REACTION BETWEEN GRIGNARD-REAGENTS AND SUBSTITUTED PYRIMIDINES [J].

ELMOGHAYAR, MRH ;

UNDHEIM, K .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1983, 37 (02) :160-162

[6] NICKEL-CATALYZED ADDITION OR COUPLING REACTIONS OF GRIGNARD-REAGENTS WITH HALOPYRIMIDINES [J].

ELMOGHAYAR, MRH ;

GROTH, P ;

UNDHEIM, K .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1983, 37 (02) :109-114

[7] HETEROCYCLES .1. A NEW ROUTE TO THE SYNTHESIS OF SUBSTITUTED 2-AMINOPYRIMIDINES [J].

ELRAYYES, NR .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (02) :415-419

[8] REACTION OF 5-BROMO- AND 2-BROMOPYRIMIDINE WITH ORGANOLITHIUM COMPOUNDS [J].

GRONOWITZ, S ;

ROE, J .

ACTA CHEMICA SCANDINAVICA, 1965, 19 (07) :1741-+

[9] ADDITION AND SUBSTITUTION-REACTIONS OF CHLOROPYRIMIDINES WITH LITHIUM REAGENTS [J].

HARDEN, DB ;

MOKROSZ, MJ ;

STREKOWSKI, L .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) :4137-4140

[10] HETEROCYCLOPOLYAROMATIC COMPOUNDS .8. FROM THE PRINCIPLE OF ARENO-ANALOGY TO HETEROCYCLOPOLYAROMATIC COMPOUNDS [J].

KAUFFMANN, T .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (01) :1-19

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