An efficient synthesis of [1,4]pyridazinooxazine[3,4-a]tetrahydro isoquinolines

被引:21
作者
Cho, SD
Park, YD
Kim, JJ
Joo, WH
Shiro, M
Esser, L
Falck, JR
Ahn, CJ
Shin, DS
Yoon, YJ [1 ]
机构
[1] Gyeongsang Natl Univ, Dept Chem, Chinju 600701, South Korea
[2] Gyeongsang Natl Univ, Life Sci Res Inst, Chinju 600701, South Korea
[3] Changwon Natl Univ, Res Inst Basic Sci, Chang Won 641773, South Korea
[4] Changwon Natl Univ, Dept Biol & Chem, Chang Won 641773, South Korea
[5] Rigaku Corp, Akishima, Tokyo 1968666, Japan
[6] Univ Texas, SW Med Ctr, Dept Biochem, Dallas, TX 75390 USA
关键词
pyridazino[4,5-b]1,4]oxazine; tetracyclic isoquinolines;
D O I
10.1016/j.tet.2004.03.011
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of fused isoquinoline-pyridazinooxazine chimera were prepared in good overall yield from phenethylamide I and 4,5-dichloropyridazin-3-one 2 via Smiles rearrangement and Pictet-Spengler cyclization. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3763 / 3773
页数:11
相关论文
共 28 条
[11]   SYNTHESIS OF SOME NON-ANTIMONIAL COMPOUNDS BIOISOSTERIC TO PRAZIQUANTEL [J].
HASSANEIN, HH ;
ELNAHAL, HM ;
GERGES, FR .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1995, 30 (06) :525-529
[12]   Synthesis and stereochemical studies of 1-and 2-phenylsubstituted 1,3-oxazino[4,3-a]isoquinoline derivatives [J].
Heydenreich, M ;
Koch, A ;
Lázár, L ;
Szatmári, I ;
Sillanpää, R ;
Kleinpeter, E ;
Fülöp, F .
TETRAHEDRON, 2003, 59 (11) :1951-1959
[13]  
Jackson AH, 1985, CHEM BIOL ISOQUINOLI, P62
[14]   Synthesis of new dihydroindeno[1,2-c]isoquinoline and indenoisoquinolinium chloride topoisomerase I inhibitors having high in vivo anticancer activity in the hollow fiber animal model [J].
Jayaraman, M ;
Fox, BM ;
Hollingshead, M ;
Kohlhagen, G ;
Pommier, Y ;
Cushman, M .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (01) :242-249
[15]   Synthesis and conformational study of 1,3,2-oxazaphosphorino[4,3-a]isoquinolines:: A new ring system [J].
Martinek, T ;
Forró, E ;
Günther, G ;
Sillanpää, R ;
Fülöp, F .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (02) :316-321
[16]  
MORITA H, 1993, CHEM PHARM BULL, V41, P1478, DOI 10.1248/cpb.41.1478
[17]  
MORITA H, 1993, CHEM PHARM BULL, V41, P1418, DOI 10.1248/cpb.41.1418
[18]   A NOVEL CONDENSED TROPONE-ISOQUINOLINE ALKALOID, PAREITROPONE, FROM CISSAMPELOS-PAREIRA [J].
MORITA, H ;
TAKEYA, K ;
ITOKAWA, H .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (06) :597-598
[19]   The reaction of isoquinoline and dimethyl acetylenedicarboxylate with 1,2-and 1,4-benzoquinones:: a novel synthesis of spiro[1,3]oxazino[2,3-a]isoquinolines [J].
Nair, V ;
Sreekanth, AR ;
Biju, AT ;
Rath, NP .
TETRAHEDRON LETTERS, 2003, 44 (04) :729-732
[20]  
Rao KA, 1997, INDIAN J CHEM B, V36, P410