Synthesis and conversions of sulfides in thiophene series

Conclusions In the action of 4 equiv of sodium in liquid ammonia on methyl 2-ethylmereapto-5-ethyl-3-thiophene-carboxylate the principal reaction product is the amide of 2-mercapto-5-ethyl-3-thiophenecarboxylic acid (III).Translated from Izvetiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2260–2265, October, 1969.     

Synthesis and some conversions of thiophene series sulfides

Condensation of 2-mercapto-5-ethyl-3-thenylamines with aromatic aldehydes and carbon disulfide gives some 2-substituted 3,4-dihydro-6-ethylthieno [3,2-e]-1,3-thizines.For Part X see [1].     

Synthesis and some transformations of thiophene series sulfides

The compound of formula C₁₀H₇N8₄, formed by the reaction of sodium-2-diethoxymethyl-3-thienylmercaptide with ammonia followed by acidification to pH 8 [1], is evidently bis(3-thiono-2-thienylidene)-dimethylamine (Ia). The action of primary amines on the thienylidenamine Ia gives N-substituted 3-mercapto-2-thienylidenimines (XIIa-c). With nickel acetate the azomethine XIIa forms an intramolecular complex (XIII).For Part XII see [1].     

Synthesis and several transformations of sulfides of the thiophene series

Several new N-substituted 2,5-bis(mercapto)-3,4-bis(iminomethyl)thiophenes, which are new tetradentate ligands of the thiophene series, were obtained by the reaction of primary amines with the product formed during the successive action of four equivalents of sodium in liquid ammonia and HCl on the tetraethylacetal of 2,5-bis(methylmercapto)-3,4-thiophenedialdehyde.For Communication XXII, see [4].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1323–1325, October, 1970.     

Synthesis and some reactions of sulfides of the thiophene series

The bromination of metal complexes of mercaptothenylide neimines of types I and II with bromine and N-bromosuccinimide leads to the cleavage of the chelate ring and the formation of the corresponding thieno [3, 2-d]-and thieno [2, 3-d]isothiazolium bromides (IIIa, b).     

Synthesis and some reactions of sulfides of the thiophene series

By the action of four equivalents of sodium in liquid ammonia on the bis(alkylmercapto)thiophenes I, II, and IX we have obtained the corresponding dimercaptothiophenes VII, IX, and VIII, which were characterizied in the form of their dibenzoyl derivatives XI–XIII. The dimercaptothiophenes VII and VIII and the o-alkylthiothiophenethiols III and IV form the internally complex compounds XIV–XVII with metal acetates.     

Synthesis and some transformations of sulfides of the thiophene series

Some 2-substituted 4-keto-2,3-dihydrothieno[3,2-e]-1,3-thiazines were obtained by condensation of 2-mercapto-5-ethylthiophene-3-carboxamide with aldehydes and ketones in the presence of gaseous HCl.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 909–910, July, 1972.     

Synthesis and some reactions of sulfides of the thiophene series

The action of two equivalents of sodium in liquid ammonia on bis(alkylthio)thiophenes of types Ia and b leads to the splitting off of the alkyl group from the sulfur atom in the -position of the thiophene ring and the formation of the corresponding -mercaptothiophenes II and III. The PMR spectra of the compounds obtained are given.For part XV, see [1].     

Synthesis and transformations of sulfides of the thiophene series. 32. Synthesis and properties of some (β-ethoxyethyl)-substituted mercapto aldimines and chelates of the thiophene series

Several N-substituted 2-mercapto-5-(-ethoxyethyl)-3-thenylidenimines and the corresponding chelate compounds with metals, which are readily soluble in organic solvents, were obtained. The synthesized compounds have a slight inhibiting effect on the liquid-phase oxidation of hydrocarbons.See [1] for Communication 31.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1331–1336, October, 1980.     

Synthesis and some transformations of sulfides of the thiophene series. X. Preparation of thienoisothiazoles from mercaptoaldimines

The action of bromine on 2-mercapto-5-alkyl-3-thienylidenimines gives thieno[3, 2-d]isothiazole bromides. 5-Ethylthieno[3, 2-d]isothiazole bromide readily splits off HBr to give 5-ethylthieno[3, 2-d]isothiazole. Lithium aluminum hydride reduces mercaptothienylideneimines to aminomethyl derivatives.     

Synthesis and transformations of sulfides of the thiophene series. 39. Synthesis and pharmacological properties of some 2,5-disubstituted 3-thienylalkylamines

A number of isomeric 3-thienylalkylamines containing methylthio and methoxy groups in the positions of the thiophene ring have been synthesized. It has been shown that they possess a weak activity of the stimulating and antidepressant type.For communication 38, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1182–1185, September, 1984.