Synthesis and reactions of some new heterocyclic compounds containing cycloalka[e]thieno[2,3-b]pyridine Moiety

Abstract

Hydrolysis of ethyl 3-amino-4-aryl-cycloalka[e]thieno[2,3-b]pyridine-2- carboxylates (3a-d) gave the corresponding o-aminocarboxylic acids 4 a-d. Heating the latter compounds (4a-d) with acetic an hydride furnished the oxazinone derivatives 5a-d which, in turn, underwent recyclization reaction to give the corresponding pyrimidinones 6a-d upon treatment with ammonium acetate in acetic acid. Reaction of 3-amino-4-aryl-cycloalka[e]thieno[2,3-b]pyridine-2- carboxamides (3f,h) with triethyl orthoformate gave pyrimidinone derivatives 7a,b. Reaction of 3-amino-4-phenyl-cycloalka[e]thieno[2,3-b]pyridine-2- carboxamides 3e,h with aromatical dehydes furnished tetrahydropyridothienopyrimidinones 8a-d. Chlorinationof 7a,b and 6a-d by using phosphorous oxychloride produced 4-chlorocycloalka[5 ,6 ]pyrido[3 ,2 :4,5]thieno[3,2-d]pyrimidine derivatives 9a-f which were used as key intermediates in the synthesis of several new cycloalkapyridothienopyrimidines 10a-f∼14a-f. Moreover, some cycloalkapyridothienotriazinones 15a,b-17a,b were synthesized.