One-pot, multicomponent route to pyrazoloquinolizinones

被引：83
作者：
Chebanov, Valentin A.
Saraev, Vyacheslav E.
Desenko, Sergey M.
Chemenko, Vitaliy N.
Shishkina, Svetlana V.
Shishkin, Oleg V.
Kobzar, Kiril M.
Kappe, C. Oliver
机构：
[1] Natl Acad Sci Ukraine, State Sci Inst, Inst Single Crystals, UA-61001 Kharkov, Ukraine
[2] Kral Franzens Univ Graz, Inst Chem, A-8010 Graz, Austria
[3] Kral Franzens Univ Graz, CDLMC, A-8010 Graz, Austria
[4] Tech Univ Munich, D-85747 Garching, Germany
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 09期
关键词：
D O I：
10.1021/ol070411l
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient synthesis of 5a-hydroxy-4,5,5a,6,7,8-hexahydropyrazolo[4,3-c]quinolizin-9-ones based on the three-component condensation of 5-aminopyrazoles, aromatic aldehydes, and cyclic 1,3-diketones is described. The multicomponent reaction is performed under strongly basic conditions applying controlled microwave heating in a sealed vessel and involves an unusual base-mediated ring-opening/recyclization of the cyclic 1,3-diketone moiety.
引用
收藏
页码：1691 / 1694
页数：4
相关论文
共 35 条
[1]   (-)-6-ALPHA-HYDROXYLUPANINE, A LUPIN ALKALOID FROM LYGOS-RAETAM VAR SARCOCARPA [J].
ABDELHALIM, OB .
PHYTOCHEMISTRY, 1995, 40 (04) :1323-1325
[2]   SYNTHESIS OF THE CIVET CONSTITUENT CIS-(6-METHYLTETRAHYDROPYRAN-2-YL)ACETIC ACID [J].
BATES, HA ;
DENG, PN .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (24) :4479-4481
[3]  
Beshitaishvili L. V., 1992, KHIM PRIR SOEDIN, V2, P240
[4]  
CHEBANOV VA, 2006, 3 INT C MULT REACT R, P52
[5]  
Chern JW, 1998, CHEM PHARM BULL, V46, P928
[6]   Metalation vs nucleophilic addition in the reactions of N-phenethylimides with organolithium reagents. Ready access to isoquinoline derivatives via N-acyliminium ions and Parham-type cyclizations [J].
Collado, MI ;
Manteca, I ;
Sotomayor, N ;
Villa, MJ ;
Lete, E .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (07) :2080-2092
[7]   TOTAL SYNTHESIS OF (+/-)-VALLESAMIDINE [J].
DICKMAN, DA ;
HEATHCOCK, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (04) :1528-1530
[8]   Structure-activity studies for a novel series of tricyclic dihydropyridopyrazolones and dihydropyridoisoxazolones as KATP channel openers [J].
Drizin, I ;
Altenbach, RJ ;
Buckner, SA ;
Whiteaker, KL ;
Scott, VE ;
Darbyshire, JF ;
Jayanti, V ;
Henry, RF ;
Coghlan, MJ ;
Gopalakrishnan, M ;
Carroll, WA .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (08) :1895-1904
[9]   Structure-activity studies for a novel series of tricyclic dihydropyrimidines as KATP channel openers (KCOs) [J].
Drizin, I ;
Holladay, MW ;
Yi, L ;
Zhang, HQ ;
Gopalakrishnan, S ;
Gopalakrishnan, M ;
Whiteaker, KL ;
Buckner, SA ;
Sullivan, JP ;
Carroll, WA .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (11) :1481-1484
[10]  
Elguero J., 2002, TARGETS HETEROCYCL S, V6, P52, DOI DOI 10.12691/WJOC-5-1-4
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