Synthesis of Some New Spirothiopyran Derivatives from the Reaction of 4-Thiopyrylidenemalononitriles with Bidentate and Active Methylene Reagents
01 Apr 2003-Phosphorus Sulfur and Silicon and The Related Elements (Taylor & Francis Group)-Vol. 178, Iss: 4, pp 863-868
TL;DR: In this paper, 2,6-Diphenyl and 2,phenyl-6-p-tolyl-4-thiopyrylidenemalomonitriles have been synthesized as f, g -unsaturated nitriles from the condensation of 2, 6-diphensyl with malononitrile.
Abstract: 2,6-Diphenyl and 2-phenyl-6-p-tolyl-4-thiopyrylidenemalomonitriles have been synthesized as f , g -unsaturated nitriles from the condensation of 2,6-diphenyl and 2-phenyl-6-p-tolyl-4H-thiopyran-4-thiones with malononitrile. Treatment of 4-thiopyrylidenemalononitriles with hydrazine hydrate, hydroxylamine hydrochloride, thiourea, thiosemicarbazide, or guanidine hydrochloride afforded the corresponding spirothiopyran derivatives of pyrazole, isoxazole, 1,3-thiazine or pyrimidine, respectively, while treatment with acetylacetone gave the corresponding spirothiopyran derivatives of pyran.
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TL;DR: New pyrrole derivatives were synthesized and assayed for their inhibitory effect on the catalytic activity of the IMP-1 MBL from Pseudomonas aeruginosa and Klebsiella pneumoniae and show micromolar inhibition constants, which range from ∼10 to 30 μM.
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TL;DR: A series of pyrrole and pyrrolopyrimidine derivatives showed promising anti hyperglycemic activity equivalent to a well-known standard antihyperglycemic drug, Glimepiride.
Abstract: A series of pyrrole and pyrrolopyrimidine derivatives were examined for their in vivo antihyperglycemic activity. Compounds Ia–c,e, and IVg showed promising antihyperglycemic activity equivalent to a well-known standard antihyperglycemic drug, Glimepiride (Amaryl, 4 mg/kg). In this paper, we examine and discuss the structure-activity relationships and antihyperglycemic activity of these compounds.
21 citations
TL;DR: In this paper, a 4th-thiazolidin-4-one was obtained by reaction of the hydrazinecarbothioamide with ethyl bromoacetate.
Abstract: The reaction of 2-[1-(naphthalen-2-yl)ethylidene]hydrazinecarbothioamide with hydrazonoyl halides afforded new thiazole derivatives, whilst reaction with compounds containing an activated double bond such as ethoxymethylene-malononitrile and benzylidenemalononitrile yielded the respective pyrimidine derivatives. A 4-thiazolidin-4-one was obtained by reaction of the hydrazinecarbothioamide with ethyl bromoacetate. Subsequent condensation of the thia-zolidinone with aromatic aldehydes afforded the corresponding arylidene derivatives. Treatment of the hydrazinecarbothioamide with dimethyl acetylenedicarboxylate resulted in the formation of a (methoxycarbonylmethylidene) thiazolinone. Reaction of the hydrazinecarbothioamide with 2-chloro-1,3-dicarbonyl compounds gave the respective thiazole derivatives. The structures of the newly synthesised compounds were confirmed by their elemental analysis and spectral data.
14 citations
TL;DR: In this article, 3-Chloro-2-phenyl-6-p-tolyl and 3-chloro 2,6-di-p tolyl-4H-thiopyran-4-ones with phosphorus pentachloride were synthesized in moderate yieldes from the reaction of 3-Tetrahydrothiopyrin-4,3-thiopyrylidene-malononitrile.
Abstract: 3-Chloro-2-phenyl-6-p-tolyl and 3-chloro-2,6-di-p-tolyl-4H-thiopyran-4-ones have been synthesized in moderate yieldes from the reaction of 3-chloro-tetrahydrothiopyran-4-ones with phosphorus pentachloride. Their thiones, oximes, and hydrazones have been also prepared. Treatment of thiones with malononitrile gave the corresponding 3-chloro-4-thiopyrylidenemalononitriles which gave 3-chloro-spirothiopyran derivatives of pyrazole, isoxazole, 1,3-thiazines when treated with hydrazine hydrate, hydroxylamine hydrochloride, thiourea and thiosemicarbazide, respectively. While treatment of 3-chloro-thiopyrylidene-malononitriles with acetylacetone gave the corresponding 3-chloro-spirothiopyran derivatives of pyran.
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TL;DR: In this article, the spectra of pyrylium perchlorate, various alkyl and aromatic derivatives, and cyanine-like dyes derived from pyryllium salts are discussed.
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