Construction of a pyrido[4,3-d]pyrimidine system on the basis of N-cyanobenzamidine and diethyl acetone-1,3-dicarboxylate

被引：6

作者：

Komkov, A. V. ^{[1
]}

Dorokhov, V. A. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2007年 / 56卷 / 11期

关键词：

N-cyanobenzamidine; diethyl acetone-1,3-dicarboxylate; nickel acetate; ethyl; 4-amino-6-ethoxycarbonylmethyl-2-phenylpyrimidine-5-carboxylate; 6-alkyl-4-amino-7-hydroxy-2-phenylpyrido[4,3-d]pyrimidin-5(6H)-ones; heterocyclization;

D O I：

10.1007/s11172-007-0361-0

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Nickel acetate promoted reaction of diethyl acetone-1,3-dicarboxylate with N-cyanobenzamidine led to ethyl 4-amino-6-ethoxycarbonylmethyl-2-phenylpyrimidine-5-carboxylate, upon treatment of which with RNH2, the corresponding 6-(carbamoylmethyl)pyrimidines were obtained. Cyclization of the latter upon treatment with MeONa afforded 6-R-4-amino-7-hydroxy-2-phenylpyrido[4,3-d]pyrimidin-5(6H)-ones.

引用

页码：2290 / 2292

页数：3

共 16 条

[1] Chemical inhibitors of protein kinases [J].

Bridges, AJ .

CHEMICAL REVIEWS, 2001, 101 (08) :2541-2571

[2] A NEW EXAMPLE OF HETEROCYCLIZATION USING CHELATES - THE SYNTHESIS OF FUNCTIONALIZED PYRIDINES FROM N,N-ACETALS OF DIACYLKETENES [J].

DOROKHOV, VA ;

GORDEEV, MF .

BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1989, 38 (12) :2638-2639

[3] SYNTHESIS OF N-UNSUBSTITUTED KETENE AMINALS FROM BETA-KETOCARBOXYLIC ESTERS AND CYANAMIDE [J].

DOROKHOV, VA ;

DEMYANETS, ZK .

RUSSIAN CHEMICAL BULLETIN, 1993, 42 (02) :384-385

[4] SYNTHESIS OF 4-AMINO-5-ALKOXYCARBONYL(ACYL)PYRIMIDINES FROM BETA-DICARBONYL COMPOUNDS AND N-CYANOAMIDINES [J].

DOROKHOV, VA ;

GORDEEV, MF ;

KOMKOV, AV ;

BOGDANOV, VS .

BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1990, 39 (01) :130-134

[5] SYNTHESIS OF DIACYLKETENE AND ALKOXYCARBONYL(ACYL)KETENE N,N-ACETALS BY THE REACTION OF BETA-DIKETONES AND BETA-KETOESTERS WITH MONOSUBSTITUTED CYANAMIDES [J].

DOROKHOV, VA ;

GORDEEV, MF ;

DEMYANETS, ZK ;

BOCHKAREVA, MN ;

BOGDANOV, VS .

BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1989, 38 (08) :1654-1659

[6]

DOROKHOV VA, 1988, STUDIES ORGANIC CHEM, V35, P253

[7] Convenient synthesis of pyrido[4,3-d]pyrimidine-2,4(1H,3H)-diones [J].

Hirota, K ;

Nakazawa, Y ;

Kitade, Y ;

Sajiki, H .

HETEROCYCLES, 1998, 47 (02) :871-882

[8] Synthesis of new pyrido[2,3-d]pyrimidine derivatives by three-component condensation of 5-acetyl-4-aminopyrimidines, cyclohexane-1,3-diones, and orthocarboxylic acid esters [J].

Komkov, A. V. ;

Prezent, M. A. ;

Ignatenko, A. V. ;

Yakovlev, I. P. ;

Dorokhov, V. A. .

RUSSIAN CHEMICAL BULLETIN, 2006, 55 (11) :2085-2090

[9] Synthesis of pyrido[2,3-d]pyrimidin-7(8H)-one derivatives from 5-acetyl-4-aminopyrimidines and β-dicarbonyl compounds [J].

Komkov, AV ;

Yakovlev, IP ;

Dorokhov, VA .

RUSSIAN CHEMICAL BULLETIN, 2005, 54 (03) :784-788

[10] EFFICIENT METHODS FOR THE SYNTHESIS OF PYRIDO[2,3-D]PYRIMIDIN-5-ONES FROM 4-AMINO-5-ACETYLPYRIMIDINES [J].

KOMKOV, AV ;

UGRAK, BI ;

BOGDANOV, VS ;

DOROKHOV, VA .

RUSSIAN CHEMICAL BULLETIN, 1994, 43 (08) :1392-1397

← 1 2 →