Application of the intramolecular aza-Wittig reaction to the synthesis of pyrido[2,3-d]pyrimidines

被引：27

作者：

Chan, J ^{[1
]}

Faul, M ^{[1
]}

机构：

[1] Amgen Inc, Chem Proc Res & Dev, Thousand Oaks, CA 91320 USA

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 20期

关键词：

tetrazolo[1,5-a]pyriditie-8-carbonyl chloride; aza-Wittig; pyrido[2,3-d]pyrimidines; iminophosphoranes;

D O I：

10.1016/j.tetlet.2006.03.091

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyrido[2,3-d]pyrimidines are synthesized in a two-step procedure from amides and tetrazolo[1,5-a]pyridine-8-carbonyl chloride. Reaction of the crude imides with triphertylphosphine effects an intramolecular aza-Wittig reaction to afford a variety of substituted pyrido[2,3-d]pyrimidines in good to moderate yields (30-76%). (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：3361 / 3363

页数：3

共 14 条

[1]

Cmoch P, 1997, MAGN RESON CHEM, V35, P237, DOI 10.1002/(SICI)1097-458X(199704)35:4<237::AID-OMR63>3.0.CO

[2]

2-L

[3]

COLLINS TL, 2004, Patent No. 075863

[4]

DUNN AD, 1986, Z CHEM, V26, P290

[5] SYNTHESIS OF NOVEL CARBOPOLYCYCLES AND HETEROPOLYCYCLES .20. SHORT-STEP SYNTHESIS OF RUTECARPINE AND TRYPTANTHRIN VIA INTRAMOLECULAR AZA-WITTIG REACTION [J].

EGUCHI, S ;

TAKEUCHI, H ;

MATSUSHITA, Y .

HETEROCYCLES, 1992, 33 (01) :153-156

[6] THE AZA-WITTIG REACTION IN HETEROCYCLIC SYNTHESIS - A REVIEW [J].

EGUCHI, S ;

MATSUSHITA, Y ;

YAMASHITA, K .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1992, 24 (02) :209-&

[7] Application of iminophosphorane-based methodologies for the synthesis of natural products [J].

Fresneda, PM ;

Molina, P .

SYNLETT, 2004, (01) :1-17

[8] HETEROCYCLES BY INTRAMOLECULAR AZA-WITTIG REACTIONS OF IMINOPHOSPHORANES OBTAINED FROM 2-AZIDOBENZOYL- AND 2-AZIDOBENZYLIDENE DERIVATIVES [J].

LUHESHI, ABN ;

SALEM, SM ;

SMALLEY, RK ;

KENNEWELL, PD ;

WESTWOOD, R .

TETRAHEDRON LETTERS, 1990, 31 (45) :6561-6564

[9]

Okawa T, 1998, SYNTHESIS-STUTTGART, P1467

[10] HETEROCYCLES, PT93 RING-OPENING REACTIONS OF SOME AZOLOAZINES AND AZINOAZINES [J].

POLLAK, A ;

POLANC, S ;

STANOVNI.B ;

TISLER, M .

MONATSHEFTE FUR CHEMIE, 1972, 103 (06) :1591-1603

← 1 2 →