Oxazepines and thiazepines. 41 . Synthesis of 4‐aryl‐2,3‐dihydro‐2‐styryl‐1,5‐benzothiazepines by the reaction of (E,E)‐cinnamylideneacetophenones with 2‐aminothiophenol and their conversion into 2,2‐disubstituted 3‐acetyl‐2,3‐dihydrobezothiazoles

New 4-aryl-2,3-dihydro-2-styryl-1,5-benzothiazepines 8–13 have been synthesized by an acid catalyzed reaction of 2-arninothiophenol (1) and (E,E)-cinnamylideneacetophenones 2–7. Ring contraction of 1,5-benzothiazepines 8–13 provided 2,2-disubstituted 3-acetyl-2,3-dihydrobenzothiazoles 14–19 under acetylating conditions.

[1]  J. Cavaleiro,et al.  Synthesis of 3-aryl-5-styryl-2-pyrazolines by the reaction of (E, E)-cinnamylideneacetophenones with hydrazines and their oxidation into pyrazoles , 2002 .

[2]  A. Levai,.  OXAZEPINES AND THIAZEPINES 39* SYNTHESIS OF TETRACYCLIC 1,5-BENZOTHIAZEPINES BY THE REACTION OF (Z)-3-ARYLIDENE-1-THIOFLAVANONES WITH 2-AMINOTHIOPHENOL , 2002 .

[3]  J. Cavaleiro,et al.  Dimethyldioxirane oxidation of (E,E)-cinnamylideneacetophenones , 2001 .

[4]  J. Elguero,et al.  Synthesis of 3‐Benzoyl‐4‐styryl‐2‐pyrazolines and Their Oxidation to the Corresponding Pyrazoles , 2000 .

[5]  A. Levai,.  Synthesis and Chemical Transformations of 1,5-Benzothiazepines , 2000 .

[6]  A. Levai,.  Optically active 1,5-benzothiazepines. , 1999, Die Pharmazie.

[7]  A. Levai,.  OXAZEPINES AND THIAZEPINES 38* SYNTHESIS OF 2,4-DIARYL-2,3-DIHYDRO-l,5-BENZOTHIAZEPINES BY THE REACTION OF 2-HYDROXYCHALCONES WITH 2-AMINOTHIOPHENOL , 1999 .

[8]  A. Levai,.  Oxazepines and Thiazepines XXXVII [1]. A Simple and Convenient Procedure for the Preparation of 3-Acyl-2,3-dihydrobenzothiazoles by Ring Contraction of 2,4-Diaryl-2,3-dihydro-1,5-benzothiazepines under Acylating Conditions , 1998 .

[9]  J. Elguero,et al.  Novel (E)‐ and (Z)‐2‐Styrylchromones from (E, E)‐2′‐Hydroxycinnamylideneacetophenones – Xanthones from Daylight Photooxidative Cyclization of (E)‐2‐Styrylchromones , 1998 .

[10]  J. Elguero,et al.  Oxidation of 4-Alkyl-2′-Hydroxy-2-cinnamylideneacetophenones with Thallium(III) Trinitrate: A New Synthesis of (E)-3-Styrylchromones , 1997 .

[11]  G. Tóth,et al.  An Efficient Procedure for the Preparation of 3‐Acetyl‐2,3‐dihydrobenzo‐thiazoles by Ring Contraction of 2,4‐Diaryl‐2,3‐dihydro‐1,5‐benzothiazepines under Acetylating Conditions , 1997 .

[12]  A. Levai,.  OXAZEPINES AND THIAZEPINES 35. SYNTHESIS OF TETRACYCLIC BENZODIAZEPINES BY THE REACTION OF 2-AMIN0THI0PHEN0L WITH EXOCYCLIC α,β-EN0NES , 1997 .

[13]  J. Cavaleiro,et al.  Syntheses of 5‐hydroxy‐2‐(phenyl or styryl)chromones and of some halo derivatives , 1996 .

[14]  A. Levai,.  OXAZEPINES AND THIAZEPINES. 32. SYNTHESIS OF TETRACYCLIC BENZOTHIAZEPINES , 1996 .

[15]  R. Gitto,et al.  Annelated 1,5-Benzothiazepines , 1995 .

[16]  J. Cavaleiro,et al.  SYNTHESIS OF 6,8-(DIBROMO OR DIIODO)-5-HYDROXY-2-(PHENYL OR STYRYL)CHROMONES , 1994 .

[17]  J. Cavaleiro,et al.  5-Hydroxy-2-(phenyl or styryl) chromones: One-pot synthesis and C-6, C-8 13C NMR assignments , 1994 .

[18]  J. Elguero,et al.  Synthesis of (E)-2-Styrylchromones , 1991 .

[19]  Y. Inada,et al.  (R)-3-[(S)-1-carboxy-5-(4-piperidyl)pentyl]amino-4-oxo-2,3,4,5- tetrahydro-1,5-benzothiazepine-5-acetic acid (CV-5975): a new potent and long-lasting inhibitor of angiotensin converting enzyme. , 1988, Japanese journal of pharmacology.

[20]  K. Hirano,et al.  Competitive enzyme immunoassay for anti-ulcer agent, (-)-cis-2,3-dihydro-3-(4-methylpiperazinylmethyl)-2-phenyl-1,5- benzothiazepin-4(5H)-one hydrochloride (BTM-1086). , 1986, Chemical & pharmaceutical bulletin.

[21]  J. Stanton,et al.  Angiotensin converting enzyme inhibitors: 1,5-benzothiazepine derivatives. , 1985, Journal of medicinal chemistry.

[22]  H. Duddeck,et al.  Oxazepines and thiazepines. XIII—conformational analysis of 2,3-dihydrobenzothiazepine derivatives† , 1982 .

[23]  A. Levai,.  Oxazepines and thiazepines. Part 12: Synthesis of 2,3-dihydro-2,4-diaryl-1,5-benzothiazepines , 1981 .

[24]  J. Grimshaw,et al.  Electrochemical reactions. Part XVII. Selective dehalogenation of styrylpyrazoline and styrylpyrazole derivatives , 1974 .

[25]  K. Ikezawa,et al.  Studies on a new 1,5-benzothiazepine derivative (CRD-401) VI. Effects on renal blood flow and renal function. , 1974, Japanese journal of pharmacology.

[26]  H. Nakajima,et al.  Studies on a new 1,5-benzothiazepine derivative (CRD-401). V. Antiarrhythmic actions. , 1973, Japanese journal of pharmacology.

[27]  T. Nagao,et al.  Studies on a new 1, 5-benzothiazepine derivative (CRD-401). II. Vasodilator actions. , 1972, Japanese journal of pharmacology.

[28]  L. Field,et al.  Notes. A Seven-Membered Heterocycle from o-Aminobenzenethiol and Chalcone , 1959 .

[29]  W. Ried,et al.  Über heterocyclische Siebenringsysteme, VIII. Synthesen Kondensierter 7‐Gliedriger Heterocyclen mit 1 Stickstoff‐ und 1 Schwefelatom , 1957 .

[30]  K. Venkataraman,et al.  122. Synthetical experiments in the chromone group. Part VI. 2-Styrylchromones , 1932 .

[31]  H. Bauer.,et al.  Ueber die Einwirkung von 50‐procentiger Eisessig‐Schwefelsäure auf das β‐benzyl‐β‐styryl‐propiophenon und seine Derivate. I , 1906 .

[32]  M. Scholtz,et al.  Synthese α,α-substituirter Pyridine. Zur Constitution des Pyridins , 1903 .

[33]  M. Scholtz.  Ueberführung aliphatischer Oxime in Pyridinderivate , 1895 .