Application of organolithium and related reagents in synthesis.: Part 22.: Synthetic strategies based on ortho-aromatic metallation.: A concise regiospecific conversion of benzoic acids into the 4-pyridyl-2H-phthalazin-1-ones.

被引:9
作者
Brzezinski, JZ [1 ]
Epsztajn, J [1 ]
Bakalarz, AD [1 ]
Lajszczak, A [1 ]
Malinowski, Z [1 ]
机构
[1] Univ Lodz, Dept Organ Chem, PL-90136 Lodz, Poland
关键词
D O I
10.1080/00397919908085788
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of phthalazin-1-ones 6, 7, 8 via the reaction of 3-hydroxyisoindolin-1-ones 3, 4, 5 with hydrazine hydrate is described. Starting compounds 3, 4, 5 were regiospecifically prepared upon the lithiation (n-BuLi) of the benzanilides 1 and subsequently the reaction of the dilithiated anilides 2 with methyl pyridinecarboxylates.
引用
收藏
页码:457 / 473
页数:17
相关论文
共 18 条
[1]   A concise regioselective synthesis of hydroxyazaisoindolinones and their conversion into pyridopyridazinones [J].
Brzezinski, JZ ;
Bzowski, HB ;
Epsztajn, J .
TETRAHEDRON, 1996, 52 (09) :3261-3272
[2]   SYNTHESIS, SALUDIURETIC, AND ANTIHYPERTENSIVE ACTIVITY OF 6,7-DISUBSTITUTED 1(2H)- AND 3,4-DIHYDRO-1(2H)-PHTHALAZINONES [J].
CHERKEZ, S ;
HERZIG, J ;
YELLIN, H .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (06) :947-959
[3]  
DUNET A, 1948, B SOC CHIM FR, P1081
[4]  
EFFENBERGER F, 1980, SYNTHESIS-STUTTGART, P151
[5]   Application of organolithium and related reagents in synthesis .18. Synthetic strategies based on aromatic metallation. A conversion of methyl ortho-pyridoylbenzoates into aza-anthra-5,10-quinones [J].
Epsztajn, J ;
Jozwiak, A ;
Krysiak, JK ;
Lucka, D .
TETRAHEDRON, 1996, 52 (33) :11025-11036
[6]   APPLICATION OF ORGANOLITHIUM AND RELATED REAGENTS IN SYNTHESIS .6. A GENERAL STUDY OF THE LITHIATION OF SECONDARY PICOLINE AMIDES AND ISONICOTINE AMIDES [J].
EPSZTAJN, J ;
JOZWIAK, A ;
CZECH, K ;
SZCZESNIAK, AK .
MONATSHEFTE FUR CHEMIE, 1990, 121 (11) :909-921
[7]   APPLICATION OF ORGANOLITHIUM AND RELATED REAGENTS IN SYNTHESIS .14. SYNTHETIC STRATEGIES BASED ON AROMATIC METALATION - A CONCISE REGIOSPECIFIC CONVERSION OF BENZOIC-ACIDS INTO THEIR ORTHO-PYRIDOYL DERIVATIVES [J].
EPSZTAJN, J ;
JOZWIAK, A ;
KRYSIAK, JA .
TETRAHEDRON, 1994, 50 (09) :2907-2916
[8]  
EPSZTAJN J, UNPUB
[9]  
ISMAIL MF, 1990, GAZZ CHIM ITAL, V120, P677
[10]  
LECHAT P, 1958, CR HEBD ACAD SCI, V246, P2771