A new and highly expedient synthesis of pyrido[2,3-d]pyrimidines

被引：68

作者：

Bagley, MC ^{[1
]}

Hughes, DD ^{[1
]}

Lloyd, R ^{[1
]}

Powers, VEC ^{[1
]}

机构：

[1] Cardiff Univ, Dept Chem, Cardiff CF10 3TB, S Glam, Wales

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 37期

关键词：

D O I：

10.1016/S0040-4039(01)01297-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2,6-Diaminopyrimidin-4-one was reacted with a number of butynones in a range of different solvents at room temperature or 60 degreesC. The Michael addition and subsequent cyclodehydration provided a new method for the synthesis of pyrido[2,3-d]pyrimidines in excellent yield without need for further purification. This new facile procedure lends itself well to combinatorial methods, providing the target heterocycle in one or two steps with total regiocontrol. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6585 / 6588

页数：4

共 25 条

[1] The synthesis of novel heterocyclic substituted α-amino acids;: further exploitation of α-amino acid alkynyl ketones as reactive substrates
Adlington, RM
Baldwin, JE
Catterick, D
Pritchard, GJ
Tang, LT
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (15): : 2311 - 2316
[2] Bagley MC, 2001, SYNLETT, P1149
[3] Diastereoselective synthesis of cis-2,5-disubstituted pyrrolidine N-oxides by the retro-Cope elimination
Bagley, MC
Tovey, J
[J]. TETRAHEDRON LETTERS, 2001, 42 (02) : 351 - 353
[4] STUDIES ON URACILS .10. A FACILE ONE-POT SYNTHESIS OF PYRIDO[2,3-D]PYRIMIDINES AND PYRAZOLO[3,4-D]PYRIMIDINES
BHUYAN, P
BORUAH, RC
SANDHU, JS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (02) : 568 - 571
[5] UBER EINE NEUE PYRIDINSYNTHESE
BOHLMANN, F
RAHTZ, D
[J]. CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (10): : 2265 - 2272
[6] NOVEL SYNTHESIS OF 2-OXO-4-PHENYL-3-BUTYNOIC ACID, A NEW INHIBITOR AND ALTERNATE SUBSTRATE OF PYRUVATE DECARBOXYLASE
CHIU, CFC
JORDAN, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) : 5763 - 5766
[7] ANTIMICROBIAL ACTIVITY OF 8-DEAZAFOLIC ACID
DEGRAW, JI
KISLIUK, RL
GAUMONT, Y
BAUGH, CM
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (04) : 470 - 471
[8] SYNTHESIS AND ANTIFOLATE PROPERTIES OF 5,10-ETHANO-5,10-DIDEAZAAMINOPTERIN
DEGRAW, JI
CHRISTIE, PH
COLWELL, WT
SIROTNAK, FM
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (02) : 320 - 324
[9] DEYANOV AB, 1991, KHIM FARM ZH+, V25, P26
[10] Approaches to combinatorial synthesis of heterocycles: Solid phase synthesis of pyridines and pyrido[2,3-d]pyrimidines
Gordeev, MF
Patel, DV
Wu, J
Gordon, EM
[J]. TETRAHEDRON LETTERS, 1996, 37 (27) : 4643 - 4646

← 1 2 3 →