An efficient hetero Diels-Alder approach to imidazo[4,5-c]pyridazines as purine analogues

被引：29

作者：

Deghati, PYF ^{[1
]}

Wanner, MJ ^{[1
]}

Koomen, GJ ^{[1
]}

机构：

[1] Univ Amsterdam, Inst Mol Chem, Organ Chem Lab, NL-1018 WS Amsterdam, Netherlands

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 25期

关键词：

Diels-Alder reaction; purines;

D O I：

10.1016/S0040-4039(98)00806-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general approach to 3-deaza-6-azapurine by a hetero Diels-Alder reaction is described. Reaction of sulfonamide protected 5-vinylimidazole with 4-phenyl-1,2,4-triazoline-3,5-dione in methanol gave the Diels-Alder adduct 8 in 85% yield. Deprotection of the resulting N-phenyltriazole was efficiently accomplished by ring opening with hydrazine followed by heating in DMSO. The completely deprotected and aromatized purine analogue 1 was obtained directly from this one-pot reaction in 48% yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4561 / 4564

页数：4

共 12 条

[1] HIGH-YIELDING SYNTHESES OF 4(5)-SUBSTITUTED IMIDAZOLES VIA ORGANOLITHIUM INTERMEDIATES - THE UTILITY OF SULFONAMIDE N-PROTECTION AND SILICON-CONTAINING BLOCKING GROUPS
CARPENTER, AJ
CHADWICK, DJ
[J]. TETRAHEDRON, 1986, 42 (08) : 2351 - 2358
[2] COREY EJ, 1973, J ORG CHEM, V38, P1973
[3] SYNTHESIS OF FLUORESCENT ADENOSINE-ANALOGS
DEBOER, RF
PETRA, DGI
WANNER, MJ
BOESAART, A
KOOMEN, GJ
[J]. NUCLEOSIDES & NUCLEOTIDES, 1995, 14 (3-5): : 349 - 352
[4] DIELS-ALDER REACTIONS OF DIAZADIENES AND CHEMISTRY OF ADDUCTS
EVNIN, AB
ARNOLD, DR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (19) : 5330 - &
[5] SYNTHESIS OF 3-(BETA-D-RIBOFURANOSYL)IMIDAZO[4,5-C]PYRIDAZINES
HALVERSON, DM
CASTLE, RN
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1974, 11 (01) : 39 - 42
[6] KOOMEN GJ, 1993, RECL TRAV CHIM PAY B, V112, P51
[7] A mild and efficient method for the selective cleavage of tert-butyldimethylsilyl ethers to alcohols
Maiti, G
Roy, SC
[J]. TETRAHEDRON LETTERS, 1997, 38 (03) : 495 - 498
[8] 2-PROTECTING GROUPS FOR 5-LITHIATION IN THE SYNTHESES OF IMIDAZOLES
NGOCHINDO, RI
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (06): : 1645 - 1648
[9] ASSIGNMENT OF ANOMERIC CONFIGURATION OF D-RIBONUCLEOSIDES, ARABINONUCLEOSIDES, 2'-DEOXYRIBONUCLEOSIDES, AND 2',3'-DIDEOXYRIBONUCLEOSIDES BY NOE DIFFERENCE SPECTROSCOPY
ROSEMEYER, H
TOTH, G
SEELA, F
[J]. NUCLEOSIDES & NUCLEOTIDES, 1989, 8 (04): : 587 - 597
[10] THE USE OF VINYL IMIDAZOLES AS DIELS-ALDER DIENES
WALTERS, MA
LEE, MD
[J]. TETRAHEDRON LETTERS, 1994, 35 (45) : 8307 - 8310

← 1 2 →