89508-14-5Relevant articles and documents
A Thiophene Analogue of Praziquantel, and Related Systems, by Intramolecular Cyclisation of Acyliminium Salts
Meth-Cohn, Otto,Vij, Rup Rani,Smalley, Robert K.,Bass, Robert J.
, p. 1001 - 1018 (2007/10/02)
N--succinimide (7a) and -glutarimide (7b) on reduction with sodium borohydride in methanol at -10 deg C yield the respective hydroxylactams which on treatment with formic acid cyclise via the intermediate acyliminium ions to 4,5,9,9a-tetrahydropyrrolothienopyridin-7-one (9a) and 4,5,8,9,10,10a-hexahydropyridothienopyridin-7-one (9b) respectively.In a similar manner, 4-cyclohexylcarbonyl-1-piperazine-2,6-dione (11) is converted into the thiophene isostere (2) of praziquantel (1).Likewise, formic acid induced cyclisations of the hydroxylactams derived from N-- (16) and N-succinimide (19) furnish 5,6,10,10a-tetrahydropyrrolothienothiazepin-8(9H)-one (18) and 5,6,10,10a-tetrahydropyrrolothienothiazepin-8(9H)-one (21), respectively.