Specific features of the reactions of quinazoline and its 4-hydroxy and 4-chloro substituted derivatives with C-nucleophiles

被引：16

作者：

Azev, Yuri A. ^{[1
,2
]}

Shorshnev, Sergey V. ^{[3
]}

Golomolzin, Boris V. ^{[1
]}

机构：

[1] Ural Sci Res Inst Technol Med Preparat, Ekaterinburg 620219, Russia

[2] Ural State Tech Univ, Dept Chem, Ekaterinburg 620002, Russia

[3] Chembridge Corp, Moscow 119435, Russia

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 24期

关键词：

Quinazoline; Nucleophiles; Transformations;

D O I：

10.1016/j.tetlet.2009.03.199

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reactions of quinazoline 1 with indole, pyrogallol and 1-phenyl-3-methylpyrazol-5-one in the presence of acid led to C-4 adducts 2, 3 and 5. Adduct 4 is formed by heating I with 1,3-dimethylbarbituric acid without acid catalysis. 1-Phenyl-3-methylpyrazol-5-one reacts with 1 without acid catalysis to form dipyrazolylmethane 6. 4-Chloroquinazoline 8 reacts with 1-phenyl-3-methylpyrazol-5-one to form 4-(1-phenyl-3-methyl-5-oxopyrazol-4-yl) quinazoline 9 and dipyrazolylmethane 6. Heating 8 with 2-methylindole leads to the formation of 4-(2-methylindol-3-yl) quinazoline 10 and tris(2-methylindol-3-yl)methane 11. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2899 / 2903

页数：5

共 12 条

[1]

ALBERT A, 1967, ANGEW CHEM, V79, P913

[2] Unusual reactions of 4,6-dichloro-5-nitropyrimidine with C-nucleophiles [J].

Azev, YA ;

Duelcks, T ;

Lork, E ;

Gabel, D .

MENDELEEV COMMUNICATIONS, 2005, 15 (05) :193-196

[3]

AZEV YA, 1995, MENDELEEV COMMUN, P229

[4] FOLATE ANTAGONISTS - 16 - ANTI-MALARIAL AND ANTIBACTERIAL EFFECTS OF 2,4-DIAMINO-6-[(HETEROCYCLIC)THIO, SULFINYL, AND SULFONYL]QUINAZOLINES .45. [J].

ELSLAGER, EF ;

JACOB, P ;

JOHNSON, J ;

WERBEL, LM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1980, 17 (01) :129-136

[5]

GOLOMOLZIN BV, 1978, ORGANIC SYNTHESIS BI, P14

[6]

GOLOMOLZIN BV, 1980, CHEM ABSTR 146713, V92

[7] SYNTHESIS AND EVALUATION OF 6-ARYLACETAMIDO-2,4-DIAMINOQUINAZOLINES AND RELATED COMPOUNDS AS FOLIC-ACID ANTAGONISTS [J].

HYNES, JB ;

ASHTON, WT .

JOURNAL OF MEDICINAL CHEMISTRY, 1975, 18 (03) :263-265

[8]

JOHNE S, 1970, PHARMAZIE, V25, P22

[9]

JOHNE S, 1981, PHARMAZIE, V36, P583

[10]

PILICHEVA TL, 1975, KHIM GETEROTSIKL+, P561

← 1 2 →