Synthesis of 4-alkyl-1(2H)-phthalazinones and 4-alkyl-2,3-benzoxazin-1-ones via ring cleavage of 3-substituted N-alkylated-3-hydroxyisoindolin-1-ones

被引:8
作者
Chun, TG
Kim, KS
Lee, S
Jeong, TS
Lee, HY
Kim, YH
Lee, WS
机构
[1] Korea Res Inst Biosci & Biotechnol, Taejon 305333, South Korea
[2] Korea Adv Inst Sci & Technol, Dept Chem, Taejon 305701, South Korea
[3] Korea Adv Inst Sci & Technol, Sch Mol Sci, Taejon 305701, South Korea
关键词
heterocycles; N-alkyl; hydrazine; phthalimide;
D O I
10.1081/SCC-120030319
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Alkyl (Me, Et, i-Pr, t-Bu)-substituted phthalimdes 5a-d were easily transformed to 1(2H)-phthalazinones 8d-i and 2,3-benzoxazin-1-ones 9d,f,and j via a one-pot addition-decyclization-cyclocondensation process.
引用
收藏
页码:1301 / 1308
页数:8
相关论文
共 16 条
[1]   2,3-BENZOXAZIN-1-ONES .1. REACTIONS OF ALUMINUM-CHLORIDE, SULFURIC-ACID, AND HYDRAZINE HYDRATE WITH 4-ARYL-2,3-BENZOXAZIN-1-ONES [J].
BADDAR, FG ;
FAHMY, AFM ;
ALY, NF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (21) :2448-2450
[2]   A concise regioselective synthesis of hydroxyazaisoindolinones and their conversion into pyridopyridazinones [J].
Brzezinski, JZ ;
Bzowski, HB ;
Epsztajn, J .
TETRAHEDRON, 1996, 52 (09) :3261-3272
[3]   Regioselective synthesis of pyrazoles via the ring cleavage of 3-substituted N-alkylated 3-hydroxyisoindolin-1-ones [J].
Chang, KT ;
Choi, YH ;
Kim, SH ;
Yoon, YJ ;
Lee, WS .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, Royal Society of Chemistry (02) :207-210
[4]   SYNTHESIS AND BIOLOGICAL EVALUATION OF SUBSTITUTED BENZO[H]CINNOLINONES AND 3H-BENZO[6,7]CYCLOHEPTA[1,2-C]PYRIDAZINONES - HIGHER HOMOLOGS OF THE ANTIHYPERTENSIVE AND ANTITHROMBOTIC 5H-INDENO[1,2-C]PYRIDAZINONES [J].
CIGNARELLA, G ;
BARLOCCO, D ;
PINNA, GA ;
LORIGA, M ;
CURZU, MM ;
TOFANETTI, O ;
GERMINI, M ;
CAZZULANI, P ;
CAVALLETTI, E .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (10) :2277-2282
[5]  
COATES WJ, 1993, SYNTHESIS-STUTTGART, P334
[6]   A new simple and convenient synthesis of 3-substituted phthalimidines [J].
Deniau, E ;
Enders, D .
TETRAHEDRON LETTERS, 2000, 41 (14) :2347-2350
[7]   GABRIEL SYNTHESIS OF PRIMARY AMINES [J].
GIBSON, MS ;
BRADSHAW, RW .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (12) :919-&
[8]  
ISMAIL MF, 1984, TETRAHEDRON, V40, P2983
[9]   Novel heterocyclic ring-expansion and/or dehydration-hydration reactions of propargylic and allenylic hydroxy γ-lactams in the presence of strong base or Lewis acid [J].
Jeong, IY ;
Lee, WS ;
Goto, S ;
Sano, S ;
Shiro, M ;
Nagao, Y .
TETRAHEDRON, 1998, 54 (48) :14437-14454
[10]  
Marcaccini S, 2001, SYNTHESIS-STUTTGART, P85