Stereoselective intramolecular hetero Diels-Alder reactions of 1-oxa-1,3-butadienes:: synthesis of novel annelated pyrrolo[1,2-a]indoles

被引:41
作者
Borah, HN [1 ]
Deb, ML [1 ]
Boruah, RC [1 ]
Bhuyan, PJ [1 ]
机构
[1] Reg Res Lab, Div Med Chem, Jorhat 785006, Assam, India
关键词
mitomycins; antitumour; antibiotic; hetero Diels-Alder reactions; oxabutadienes;
D O I
10.1016/j.tetlet.2005.03.091
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel classes of pyrano-1,3-dioxane-, pyranopyrimidine- and pyranopyrazole-fused pyrrolo[1,2-a]indoles are synthesised via stereoselective intramolecular 1-oxa-1,3-butadiene hetero Diels-Alder reactions. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3391 / 3393
页数:3
相关论文
共 14 条
[1]  
[Anonymous], 1985, ALKALOIDS CHEM BIOL
[2]   SYNTHESIS OF DIHYDROISOXAZOLO AND TETRAHYDROISOXAZOLO[3',4'-3,4]PYRROLO[1,2-A]INDOLES VIA INTRAMOLECULAR CYCLO-ADDITIONS - A NOVEL CLASS OF MITOMYCIN ANALOGS [J].
BHUYAN, PJ ;
BORUAH, RC ;
SANDHU, JS .
TETRAHEDRON LETTERS, 1989, 30 (11) :1421-1422
[3]  
Boger D. L., 1987, HETERO DIELS ALDER M, P34
[4]   Recent developments in imino Diels-Alder reactions [J].
Buonora, P ;
Olsen, JC ;
Oh, T .
TETRAHEDRON, 2001, 57 (29) :6099-6138
[5]  
CARTER SK, 1979, MITOMYCIN C
[6]  
Daly JW., 1986, ALKALOIDS CHEM BIOL, P1
[7]   A STEREOSPECIFIC ROUTE TO AZIRIDINOMITOSANES - THE SYNTHESIS OF NOVEL MITOMYCIN CONGENERS [J].
DANISHEFSKY, S ;
BERMAN, EM ;
CIUFOLINI, M ;
ETHEREDGE, SJ ;
SEGMULLER, BE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3891-3898
[8]  
DEMISING G, 1975, CHEM REV, V75, P651
[9]   Studies on uracils:: a facile one-pot synthesis of oxazino[4,5-d]-, pyrano[2,3-d]-, pyrido[2,3-d]- and pyrimido[4,5-d]pyrimidines using microwave irradiation in the solid state [J].
Devi, I ;
Borah, HN ;
Bhuyan, PJ .
TETRAHEDRON LETTERS, 2004, 45 (11) :2405-2408
[10]   SYNTHESIS OF MITOMYCIN-C ANALOGS .1. INTRODUCTION OF THE URETHANE FUNCTION AT C-10 OF THE PYRROLO[1,2-A]INDOLE SKELETON [J].
DIJKSMAN, WC ;
VERBOOM, W ;
EGBERINK, RJM ;
REINHOUDT, DN .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (20) :3791-3797