Reaction of 6‐phenyl‐2‐(p‐toluenesulfonyl)‐3(2H)pyridazinone with grignard reagents

作者: Choji Kashima , Akira Katoh , Miyuki Fukasawa , Yoshimori Omote

DOI: 10.1002/JHET.5570220362

关键词: Grignard reagentQuenching (fluorescence)Nuclear magnetic resonance spectroscopyReaction conditionsOrganic chemistryReagentChemistryAliphatic compoundAlcohol

摘要: 6-Phenyl-2-(p-toluenesulfonyl)-3(2H)pyridazinone (I) reacted with Grignard reagents to give 5-substituted 4,5-dihydro-3(2H)pyridazinones II and two types of dihydropyridazines, III IV. The ratio II, III, IV was sensitively dependent on the reaction conditions. Further, by quenching mixture alcohol, ring-opened product VII mainly isolated.

参考文章(8)
CHOJI KASHIMA, AKIRA KATOH, YUKO YOKOTA, YOSHIMORI OMOTE, Ring Transformation Reaction of 1, 4, 6-Trisubstituted 2 (1H)-Pyrimidinones and -Thiones with Hydroxylamine Chemical & Pharmaceutical Bulletin. ,vol. 29, pp. 2516- 2519 ,(1981) , 10.1248/CPB.29.2516
CHOJI KASHIMA, AKIRA KATOH, YUKO YOKOTA, YOSHIMORI OMOTE, Dimroth-Type Ring Transformation of 1, 4, 6-Trisubstituted-2 (1H)-Pyrimidinethiones with Ammonia and Primary Alkyl Amines Chemical & Pharmaceutical Bulletin. ,vol. 30, pp. 1942- 1946 ,(1982) , 10.1248/CPB.30.1942
A. K. Fateen, A. H. Moustafa, A. M. Kaddah, N. A. Shams, Different Regioselective Behaviour of Organolithium and Organomagnesium Reagents toward Pyridazine Derivatives Synthesis. ,vol. 1980, pp. 457- 460 ,(1980) , 10.1055/S-1980-29050
Choji Kashima, Akira Katoh, Yuko Yokota, Yoshimari Omote, Ring opening reaction of 3,6-Dihydro-2-(1H)pyrimidinones with hydroxylamine hydrochloride Journal of Heterocyclic Chemistry. ,vol. 18, pp. 1469- 1470 ,(1981) , 10.1002/JHET.5570180737
C. KASHIMA, SYNTHETIC REACTIONS USING ISOXAZOLE COMPOUNDS ChemInform. ,vol. 11, pp. 1343- ,(1979) , 10.1002/CHIN.198011399
Choji Kashima, Akira Katoh, Nobutoshi Yoshiwara, Yoshimori Omote, Preparation of N-aryl-2,4-diaminopentanes by the ring opening reaction of 1-aryl-3,4,5,6-tetrahydro-2-(1H)pyrimidinones Journal of Heterocyclic Chemistry. ,vol. 18, pp. 1595- 1596 ,(1981) , 10.1002/JHET.5570180821
AKIRA KATOH, YOSHIMORI OMOTE, CHOJI KASHIMA, Ring Transformation Reactions of 1-Substituted 2 (1H)-Pyrimidinones and Related Compounds with Active Methylene Compounds Chemical & Pharmaceutical Bulletin. ,vol. 32, pp. 2942- 2946 ,(1984) , 10.1248/CPB.32.2942
Robert H. Shapiro, Marsha J. Heath, Tosylhydrazones. V. Reaction of Tosylhydrazones with Alkyllithium Reagents. A New Olefin Synthesis. Journal of the American Chemical Society. ,vol. 89, pp. 5734- 5735 ,(1967) , 10.1021/JA00998A601