SYNTHESIS OF THIENOQUINOLINES .2. SYNTHESIS OF NOVEL TETRAHYDROQUINOLINO[3',2'-4,5]THIENO[3,2-D]PYRIMIDINE DERIVATIVES

The key compound, 11-p-chlorophenyl-7, 8, 9, 10-tetrahydroquinolino[3′, 2′:4, 5]thieno[3, 2-d]pyrimidin-4(3H)-one (2) was prepared and reacted with methyl iodide to give the N-methyl derivative (3). Also, reaction of 2 with phosphours oxychloride yielded 4-chloro-ll-p-chlorophenyl-7, 8, 9, 10-tetrahydroquin-olino[3′, 2′:4, 5]thieno[3, 2-d]pyrimidine (4) which, in turn, underwent reactions with thiourea, aniline, piperidine, morpholine, 1-methylpiperazine and/or hydrazine hydrate to afford the corresponding 4-substituted pyrimidine derivatives 5, 7, 8, 9, 10 and 11 respectively, Methylation of 5 yielded thioether 6. Furthermore, reaction of 4 with sodium azide gave tetrazolo derivative 12 which was also obtained by diazotisation of 11. The structure of all new compounds was confirmed by elemental and spectral analyses (ir, nmr). © 1992, Taylor & Francis Group, LLC. All rights reserved.