Synthesis of pyrido[2,3-d]pyrimidines via palladium-catalyzed reaction of iodouracil with acetylenes

被引：12

作者：

Bae, JW ^{[1
]}

Lee, SH ^{[1
]}

Cho, YJ ^{[1
]}

Jung, YJ ^{[1
]}

Hwang, HJ ^{[1
]}

Yoon, CM ^{[1
]}

机构：

[1] Korea Univ, Grad Sch Biotechnol, Dept Life Sci & Biotechnol, Sungbuk Ku, Seoul 136701, South Korea

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 31期

关键词：

iodouracil; acetylene; palladium acetate; LiCl; pyridopyrimidine;

D O I：

10.1016/S0040-4039(00)00964-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of iodouracils having a formamidine or acetamidine moiety 1 with various acetylenes 2 in DMF at 120 degrees C using potassium carbonate and a catalytic amount of palladium acetate gave a mixture of pyrido[2,3-d]pyrimidine derivatives in good to high yields. Addition of lithium chloride to the reaction solution resulted in a change of reaction selectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：5899 / 5902

页数：4

共 13 条

[1] SYNTHESIS AND ANTI-TUMOR ACTIVITY OF 2,4-DIAMINO-6-(2,5-DIMETHOXYBENZYL)-5-METHYLPYRIDO[2,3-D]PYRIMIDINE
GRIVSKY, EM
LEE, S
SIGEL, CW
DUCH, DS
NICHOL, CA
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1980, 23 (03) : 327 - 329
[2] Palladium-catalyzed cyclocarbonylation of o-iodophenols and 2-hydroxy-3-iodopyridine with heterocumulenes:: Regioselective synthesis of benzo[e]-1,3-oxazin-4-one and pyrido[3,2-e]-1,3-oxazin-4-one derivatives
Larksarp, C
Alper, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (25) : 9194 - 9200
[3] Synthesis of polycyclic aromatic hydrocarbons by the Pd-catalyzed annulation of alkynes
Larock, RC
Doty, MJ
Tian, QP
Zenner, JM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) : 7536 - 7537
[4] SYNTHESIS OF AROMATIC HETEROCYCLES VIA PALLADIUM-CATALYZED ANNULATION OF INTERNAL ALKYNES
LAROCK, RC
YUM, EK
DOTY, MJ
SHAM, KKC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11) : 3270 - 3271
[5] SYNTHESIS OF INDENONES VIA PALLADIUM-CATALYZED ANNULATION OF INTERNAL ALKYNES
LAROCK, RC
DOTY, MJ
CACCHI, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (17) : 4579 - 4583
[6] Synthesis of α-pyrones via palladium-catalyzed annulation of internal alkynes
Larock, RC
Han, XJ
Doty, MJ
[J]. TETRAHEDRON LETTERS, 1998, 39 (32) : 5713 - 5716
[7] SYNTHESIS OF INDOLES VIA PALLADIUM-CATALYZED HETEROANNULATION OF INTERNAL ALKYNES
LAROCK, RC
YUM, EK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (17) : 6689 - 6690
[8] Intramolecular nucleophilic addition of vinylpalladiums to aryl ketones
Quan, LG
Gevorgyan, V
Yamamoto, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (14) : 3545 - 3546
[9] Palladium catalyzed co-trimerization of benzyne with alkynes. A facile method for the synthesis of phenanthrene derivatives
Radhakrishnan, KV
Yoshikawa, E
Yamamoto, Y
[J]. TETRAHEDRON LETTERS, 1999, 40 (42) : 7533 - 7535
[10] THE CHEMISTRY OF METHOTREXATE AND ITS ANALOGS
RAHMAN, LKA
CHHABRA, SR
[J]. MEDICINAL RESEARCH REVIEWS, 1988, 8 (01) : 95 - 155

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