A synthetic approach to 1,3,4-thiadiazolidine-2-thiones

Heugebaert, F. C.; Willems, Jelmer

doi:10.1016/0040-4020(66)80065-0

Cited by 20 publications

(4 citation statements)

References 13 publications

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“…Synthesis . Schiff base condensation of dithiocarbazic acids generates thiadiazoline-2-thione derivatives by an internal ring closure reaction . These heterocyclic products, on being treated with metal ions, undergo ring opening to produce the metal complexes of the corresponding Schiff base ligand (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Oxovanadium(V) and Cobalt(III) Complexes of Dithiocarbazate-Based Schiff Base Ligands: Formation of a Thiadiazole Ring by Vanadium-Induced Cyclization of the Coordinated Ligand

et al. 2002

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S-Methyl 3-((2-hydroxyphenyl)methyl)dithiocarbazate (H(2)L(1)) and its bromo derivative (H(2)L(2)), which are traditionally biprotic tridentate (ONS) ligands, behave in an unprecedented manner when allowed to react with [VO(acac)(2)] under an oxidative environment in acetonitrile-water medium containing a catalytic amount of alkali metal ion. The products obtained are oxovanadium(V) compounds [VOL(L(cyclic))] (L = L(1), 1a, and L(2), 1b) that contain one molecule of ligand which undergoes metal-induced cyclization to form a thiadiazole ring. Compound 1a crystallizes in the triclinic space group P(-)1 with a = 9.1830(9) A, b = 9.4165(12) A, c = 12.700(2) A, alpha = 100.988(8)(o), beta = 100.195(7)(o), gamma = 78.774(8)(o), V = 1046.3(2) A(3), and Z = 2. With cobalt(III), however, the products [CoL(HL)].H(2)O (L = L(1), 2a, and L(2), 2b) have hydrogen-bonded dimeric structures with each ligand virtually carrying 1.5 units of negative charge as confirmed by X-ray crystal structure analysis of 2a. It also crystallizes in triclinic space group P(-)1 with a = 12.0842(8) A, b = 13.5251(9) A, c = 14.1960(10) A, alpha = 78.122(6)(o), beta = 73.888(6)(o), gamma = 78.255(6)(o), V = 2154.7(3) A(3), and Z = 4. In solution, 2a is a symmetric molecule as indicated by (1)H NMR, involving a characteristic hydrogen-bonded O-H-O broad feature in the downfield (at 14.5 ppm) connecting both monoprotonated (LH(-)) and deprotonated (L(2-)) forms of the ligand--a situation somewhat analogous to the classic H-F-H case as observed in bifluoride ion.

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Section: Resultsmentioning

confidence: 99%

Oxovanadium(V) and Cobalt(III) Complexes of Dithiocarbazate-Based Schiff Base Ligands: Formation of a Thiadiazole Ring by Vanadium-Induced Cyclization of the Coordinated Ligand

et al. 2002

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“…Описана також взаємодія гідразонів 97 із ізо-ціанатом калію [59], роданідом калію [60] та сір-ковуглецем [61], яка приводить до азольних спо-лук 98-100 (схема 34).…”

Section: -гібридизованого атома вуглецю та атома азотуunclassified

Reactions of N-alkylhydrazones of aliphatic ketones

Kurpil¹,

Ivonin²,

Volochnyuk³

2014

J. org. pharm. chem.

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“…Employing the one-pot method of Busch, 26 reaction of carbon disulfide, hydrazine hydrate, and alkyl halides 10 in the presence of base generated the corresponding S-alkyl dithiocarbazates 11, which underwent condensation with aldehydes and ketones 12 to generate hydrazones 15 as single diastereomers. Alternatively, treatment of hydrazones 13 with carbon disulfide generated 1,3,4-thiadiazolidine-2-thiones 14, 27 which underwent ring-opening and exclusive S-alkylation to generate 15. While alkylthio(thiocarbonyl)hydrazones can potentially exist in equilibrium with 2,3-dihydro-1,3,4-thiadiazoles 16, no evidence for the presence of such S,N-acetals was found in the 13 C NMR spectra of these products, which display characteristic carbodithioate and hydrazone signals at approximately 200 and 150 ppm, respectively.…”

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2-Arylidene Hydrazinecarbodithioates as Potent, Selective Inhibitors of Cystathionine γ-Lyase (CSE)

Bhattacharjee

Sinha

Ratia

et al. 2017

ACS Med. Chem. Lett.

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Hydrogen sulfide is produced from l-cysteine by the action of both cystathionine γ-lyase (CSE) and cystathionine β-synthase (CBS) and increasingly has been found to play a profound regulatory role in a range of physiological processes. Mounting evidence suggests that upregulation of hydrogen sulfide biosynthesis occurs in several disease states, including rheumatoid arthritis, hypertension, ischemic injury, and sleep-disordered breathing. In addition to being critical tools in our understanding of hydrogen sulfide biology, inhibitors of CSE hold therapeutic potential for the treatment of diseases in which increased levels of this gasotransmitter play a role. We describe the discovery and development of a novel series of potent CSE inhibitors that show increased activity over the benchmark inhibitor and, importantly, display high selectivity for CSE versus CBS.

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A synthetic approach to 1,3,4-thiadiazolidine-2-thiones

Cited by 20 publications

References 13 publications

Oxovanadium(V) and Cobalt(III) Complexes of Dithiocarbazate-Based Schiff Base Ligands: Formation of a Thiadiazole Ring by Vanadium-Induced Cyclization of the Coordinated Ligand

Oxovanadium(V) and Cobalt(III) Complexes of Dithiocarbazate-Based Schiff Base Ligands: Formation of a Thiadiazole Ring by Vanadium-Induced Cyclization of the Coordinated Ligand

Reactions of N-alkylhydrazones of aliphatic ketones

2-Arylidene Hydrazinecarbodithioates as Potent, Selective Inhibitors of Cystathionine γ-Lyase (CSE)

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