New synthetic approach to [1]benzopyrano[4,3-b]pyridin-5-one derivatives

被引：20
作者：
Beccalli, EM
Contini, A
Trimarco, P
机构：
[1] Univ Milan, Ist Chim Organ A Marchesini, Fac Farm, I-20133 Milan, Italy
[2] Univ Milan, Ctr Interuniv Ric Reaz Pericicliche & Sintesi Sis, I-20133 Milan, Italy
来源：
TETRAHEDRON LETTERS | 2004年 / 45卷 / 17期
关键词：
3-formylcoumarin amidines; aldols; 1]benzopyrano-[4,3-b]pyridin-5-ones; intramolecular cyclization;
D O I：
10.1016/j.tetlet.2004.03.009
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new synthesis of [1]benzopyrano[4,3-b]pyridin-5-ones 4 was developed starting from 3-formyl-coumarin N-functionalized amidines 3. The reaction is based likely on the intramolecular cyclocondensation of the C-alpha amidinic carbanion in basic medium on the formyl group. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3447 / 3449
页数：3
相关论文
共 19 条
[1]   An effective contribution to functionalized pyridines synthesis by way of an unusual rearrangement of amidines [J].
Beccalli, EM ;
Contini, A ;
Trimarco, P .
TETRAHEDRON, 2002, 58 (06) :1213-1221
[2]   3-nitrocoumarin amidines:: A new synthetic strategy for substituted [1]benzopyrano[3,4-d]imidazol-4(3H)-ones [J].
Beccalli, EM ;
Contini, A ;
Trimarco, P .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (20) :3976-3984
[3]  
BOYD GV, 1991, CHEM AMIDINES IMIDAT, V2, P370
[4]  
BRAUNINGER H, 1986, NATURWISSENSCHAFTLIC, V35, P34
[5]  
BROEKHOF NLJM, 1979, TETRAHEDRON LETT, P2433
[6]  
DEWOLFE RH, 1975, CHEM AMIDINES IMIDAT, P350
[7]   A FACILE NEW SYNTHESIS OF ALDEHYDE ENAMINES IN HIGH-YIELD AND HIGH-PURITY [J].
FISHER, GB ;
LEE, L ;
KLETTKE, FW .
SYNTHETIC COMMUNICATIONS, 1994, 24 (11) :1541-1546
[8]   REACTIONS WITH HETEROCYCLES CONTAINING A 2-ACYL-2-PROPENONE STRUCTURE .3. PYRIDO[3,2-C] COUMARINS FROM 3-SUBSTITUTED 1-BENZOPYRANS AND ENAMINES [J].
HEBER, D .
ARCHIV DER PHARMAZIE, 1987, 320 (05) :402-406
[9]   THE VILSMEIER REACTION IN THE SYNTHESIS OF 3-SUBSTITUTED [1]BENZOPYRANO[4,3-B]PYRIDIN-5-ONES - AN UNUSUAL PYRIDINE RING-CLOSURE [J].
HEBER, D ;
IVANOV, IC ;
KARAGIOSOV, SK .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1995, 32 (02) :505-509
[10]   SYNTHESIS OF 5H-[1]BENZOPYRANO[4,3-B]PYRIDIN-5-ONES CONTAINING AN AZACANNABINOIDAL STRUCTURE [J].
HEBER, D ;
BERGHAUS, T .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1994, 31 (06) :1353-1359
12