The Preparation of 4,5-Dihydro-5-Phenyl-5-(2-Phenylethenyl)Isoxazoles, 4,5-Dihydro-5-Methyl-5-(2-Phenylethenyl)Isoxazoles, or 4,5-Dihydro-5,5-DI-(2-Phenylethenyl)Isoxazoles from Dilithiated C(α),O-Oximes and Select α,β–-Unsaturated Ketones

作者: Jessica D. Townsend , Wayne Kelley , Kelly L. Rose , Deborah A. Schady , Jennifer R. Downs

DOI: 10.1080/00397910008087396

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摘要: Abstract C(α),O-oximes were dilithiated with lithium diisopropylamide and condensed three α,β-unsaturated ketones: (2E)-1,3-diphenyl-2-propen-1-one, or (1E, 4E)-1,5-diphenyl-1,4-pentadien-3-one, (3E)-4-phenyl-3-buten-2-one, followed by immediate acid cyclization to variously substituted 4,5-dihydroisoxazoles: 4,5-dihydro-5-phenyl-5-(2-phenylethenyl)isoxazoles, 4,5-dihydro-5-methyl-5-(2-phenylethenyl)isoxazoles, 4,5-dihydro-5,5-di-(2-phenylethenyl)-isoxazoles.

参考文章(38)
Tammy D. Fulmer, Lisette P. Dasher, Bonni L. Bobb, Jana D. Wilson, Kimberly L. Sides, Charles F. Beam, An improved synthesis of 3,5-disubstituted isoxazoles and pyrazoles from C(α),O-dilithiooximes and C(α),N-dilithiophenylhydrazones Journal of Heterocyclic Chemistry. ,vol. 17, pp. 799- 800 ,(1980) , 10.1002/JHET.5570170437
Alan R Katritzky, Charles W Rees, Eric FV Scriven, None, Comprehensive heterocyclic chemistry II Pergamon. ,(1996)
Janusz Baran, Herbert Mayr, Mechanistic impact of oxime formation accompanying 1,3-dipolar cycloadditions of nitrile oxides Journal of Organic Chemistry. ,vol. 54, pp. 5012- 5016 ,(1989) , 10.1021/JO00282A012
Osamu Moriya, Yoshikiyo Urata, Takeshi Endo, Dehydrochlorination of hydroximoyl chlorides by the use of vinyltins for synthesis of isoxazolines (dihydrooxazoles) Journal of The Chemical Society, Chemical Communications. pp. 884- 885 ,(1991) , 10.1039/C39910000884
Otohiko Tsuge, Shuji Kanemasa, Norihiko Nakagawa, Hiroyuki Suga, Horner–Emmons Olefination of 4-Hydroxy-2-oxoalkylphosphonates and Related Compounds: Applications to the Syntheses of (±)-Gingerol, (±)-Yashabushiketol, and (±)-Dihydroyashabushiketol Bulletin of the Chemical Society of Japan. ,vol. 60, pp. 4091- 4098 ,(1987) , 10.1246/BCSJ.60.4091
G. Clayton Bassler, Robert Milton Silverstein, Spectrometric identification of organic compounds ,(1963)
Charles F. Beam, Morgan C. D. Dyer, Richard A. Schwarz, Charles R. Hauser, New synthesis of isoxazoles from 1,4-dianions of oximes having an .alpha. hydrogen. Mass spectrometry Journal of Organic Chemistry. ,vol. 35, pp. 1806- 1810 ,(1970) , 10.1021/JO00831A020
Charles A. Park, Charles F. Beam, Edwin M. Kaiser, Robert J. Kaufman, Fred E. Henoch, Charles R. Hauser, Preparation of 2‐isoxazolines from C(α),O‐dilithiooximes and aldehydes and ketones Journal of Heterocyclic Chemistry. ,vol. 13, pp. 449- 453 ,(1976) , 10.1002/JHET.5570130306
Osamu Moriya, Hideo Takenaka, Yoshikiyo Urata, Takeshi Endo, Synthesis of isoxazolines and isoxazoles via generation of nitrile oxides from O-stannyl aldoximes Journal of the Chemical Society, Chemical Communications. pp. 1671- 1672 ,(1991) , 10.1039/C39910001671