102254-56-8Relevant articles and documents
Saturated Heterocycles, 75 - Preparation of Tetracyclic Thiophene Derivatives with Bridgehead Nitrogen. Synthesis of Polymethylenethienodihydropyrrolo-, tetrahydropyrido- and tetrahydroazepinopyrimidin-4-ones and -4-thiones
Csukonyi, Katalin,Lazar, Janos,Bernath, Gabor,Hermecz, Istvan,Meszaros, Zoltan
, p. 1295 - 1303 (2007/10/02)
The following tetracyclic ring systems and their derivatives have been synthesized for pharmacological investigations: Trimethylenethienodihydropyrrolopyrimidin-4-one and -4-thione (1a, 5a); Tetramethylenethienodihydropyrrolopyrimidin-4-one and -4-thione (1b, 1j, 5b); Pentamethylenethienodihydropyrrolopyrimidin-4-one and-4-thione (1c, 5c); Trimethylenethienotetrahydropyridopyrimidin-4-one and -4-thione (1d, 5d); Tetramethylenethienotetrahydropyridopyrimidin-4-one and -4-thione (1e, 5e);Pentamethylenethienotetrahydropyridopyrimidin-4-one and -4-thione (1f, 5f); Trimethylenethienotetrahydroazepinopyrimidin-4-one and -4-thione (1g,5g); Tetramethylenethienopyrimidin-4-one and -4-thione (1h, 5h); Pentamethylenethienotetrahydroazepinopyrimidin-4-one and -4-thione (1i, 5i); Tetramethylenethienotetrahydroazepinopyrimidin-4-one (7b); Pentamethylenethieno-tetrahydropyridopyrimidin-4-one (7c).Compounds 1a-i were synthesized from 2-amino-3-ethoxycarbonyl-4,5-polymethylenethiophene 2a-c with the corresponding lactim ethers (3a-c) in chlorobenzene in the presence of polyphosphoric acid (PPA).Compounds 7b and 7c were obtained in the reaction ob β-amino acid esters 2a and 2c with 2-bromopyridine (6).The thione derivatives (5a-i) were prepared from compounds 1a-i with phosphorus(V) sulphide. - Keywords: Condensation of 2-amino-3-ethoxycarbonyl-4,5-polymethylenethiophene with lactim ethers and 2-bromopyridine; Oxo-thio exchange