Degradational cyclization of α-[2-phenyl-2- (phenylsulfonylhydrazono)ethyl]phenacylidenetriphenylphosphoranes to 3,6- diphenylpyridazines and 5-benzoyl-3-phenylpyrazoles

Heterocycles

Volumn 51, Issue 12, 1999, Pages 2949-2960

  Ito, Suketaka ^a   Kakehi, Akikazu ^a   Okada, Kyoko ^a  

^a SHINSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA [2 PHENYL 2 (PHENYLSULFONYLHYDRAZONO)ETHYL]PHENACYLIDENETRIPHENYLPHOSPHORANE DERIVATIVE; BENZENESULFONIC ACID DERIVATIVE; BROMINE DERIVATIVE; PHENYLHYDRAZONE DERIVATIVE; PHOSPHINE OXIDE DERIVATIVE; PHOSPHORANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DEGRADATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 0033396737     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-99-8733     Document Type: Article

References (30)

1. Present address: Kao Corporation, Research and Development Labolatories, 1334 Minato, Wakayama 640-8404, Japan.
2. The base-induced 1,4-elimination of hydrogen halide is known to take place in arylsulfonylhydrazones of α-halo ketones, which results in the formation of arylsulfonylazoethylenes: see, G. Mossa and L. Caglioti, J. Chem. Soc. B, 1968, 1404; L. Caglioti and G. Rosini, Chem. Ind. (London), 1969, 1093.
3. The base-induced 1,4-elimination of hydrogen halide is known to take place in arylsulfonylhydrazones of α-halo ketones, which results in the formation of arylsulfonylazoethylenes: see, G. Mossa and L. Caglioti, J. Chem. Soc. B, 1968, 1404; L. Caglioti and G. Rosini, Chem. Ind. (London), 1969, 1093.
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6. S. Ito, A. Kakehi, K. Okada, S. Goto, and H. Kawaguchi, Heterocycles, 1997, 45, 889.
7. The reaction of phenacyl bromide, the precursor of 1a, with phenacylidenetriphenylphosphorane (2a) was reported. However, this reaction did not give α -(phenacyl)phenacylidenetriphenylphosphorane corresponding to 4a but 1,2-dibenzoylethylene and 1,2,3-tribenzoylcyclopropane were obtained along with phenacyltriphenylphosphonium bromide (3a): see, M. Siemiatycki and H. Strezelecka, Compt. rend., 1960, 250, 3489.
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19. -1 (KBr); see Ref. 13b.
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23. A single crystal of 4d and of 4g for the X-Ray analysis could not be obtained.
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25. 2: C, 82.73; H, 5.21; N, 12.06%. Found: C, 82.70; H, 5.22; N, 12.08%.
26. -1: A. Zecchina, L. Cerruti, S. Coluccia, and E. Borello, J. Chem. Soc. B, 1967, 1363.
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29. F. Ramirez and S. Dershowitz, J. Org. Chem., 1957, 22, 41; A. V. Dombrovskii and M. I. Shevchuk, Zh. Obshch. Khim., 1963, 33, 1235.
30. C tables have been deposited at the Cambridge Crystallographic Data Centre.