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Yunus Akcamur, G. Penn, E. Ziegler, H. Sterk, G. Kollenz, K. Peters, E. Peters, H. Schnering (1986)
Reaktionen mit cyclischen Oxalylverbindungen, XXIV. Zur Reaktion von 4-Benzoyl-5-phenyl-furan-2,3-dion mit Phenylhydrazonen bzw. PhenylhydrazinMonatshefte für Chemie / Chemical Monthly, 117
S. El-kousy, A. El-Torgoman, A. El-Basiouny, A. Hashem (1988)
Synthesis and reactions of some Δβ,γ-butenolides with a study of their biological activityPharmazie, 43
Chemistry of Heterocyclic Compounds, Vol. 39, No. 4, 2003 SYNTHESIS OF 4-(1,5-DIMETHYL-3-OXO- 2-PHENYL-2,3-DIHYDRO-1H-PYRAZOL-4-YLIMINO)- 6-PHENYL-1,4-DIHYDRO-2H-PYRIDAZIN-3-ONES A. E. Rubtsov and V. V. Zalesov Keywords: 3-imino-2-furanones, 4-imino-3-pyridazinones, substituted hydrazines. We have found that 1,5-dimethyl-4-(2-oxo-5-phenyl-3-furanylideneamino)-2-phenyl-1,2-dihydro-3- pyrazolone ( ) (the synthesis of was described in our previous work [1]) reacts with methyl-, ethyl-, and 1 1 phenylhydrazines or with 1,2-diphenylhydrazine in an inert solvent with recyclization to form 4-(1,5-dimethyl- 3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylimino)-6-phenyl-1,4-dihydro-2H-pyridazin-3-ones 2: Ph Ph Ph O Ph 1 2 R NHNHR Me N Me N 1 – H O N Me Me O O 1 2a–c 1 1 2 2 2 2 a-c R = H, d R = Ph; a R = Me, b R = Et, c, d R = Ph The formation of compounds 2 probably proceeds through opening of the furan ring after attack of the hydrazine amino group at furanone C atom. The intermediate formed cyclizes through attack of the (2) secondary amino group –NHR at C atom with simultaneous splitting of water. A similar recyclization has 2 (5) been considered in the reactions of hydrazines with structurally-similar 4,5-disubstituted 2,3-furandiones [2, 3] and 3-methylene-(3H)-furan-2-ones [4]. Pyridazinones 2 are colorless crystalline compounds obtained in yields ranging from 64 to 92%. The
Chemistry of Heterocyclic Compounds – Springer Journals
Published: Oct 5, 2004
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