Tramps like Us: Music and Meaning among Springsteen Fans

Facile Synthesis of Fluorinated Purines and Thiapurines

“…7-(4-Methoxyphenyl)-2-morpholin-4-yl-7-(trifluoromethyl)-6,7-dihydro[1,3]thiazolo[4,5-d 27;H,4.13;N,13.52. Found: C,49.30;H,4.12;N,13.53.…”

“…These intermediates underwent a 6-exo-trig cyclisation (toluene, reflux) to give the 5-(trifluoromethyl) [1,3]thiazolo[4,5-d]pyrimidin-7(6H)-ones 16 and 2-(trifluoromethyl)-1,9-dihydro-6H-purin-6-one 18 in 83-91% yield. The structures and composition of compounds 16 were corroborated through 1 H, 13 C and 19 F NMR spectroscopy, and elemental analysis.…”

“…Thiazolo [4,5-d]pyrimidines, which are thia analogues of the purine ring system, have been widely utilised as starting materials for the synthesis of thiaadenosine analogues. 12 Various derivatives of 3-b-D-ribofuranosyl [1,3]thiazolo [4,5-d]pyrimidine are clinically used as immunomodulators, 13 inhibitors of HCV replication, 14 and antiviral 15 and antitumor agents. 16 Reactions of 1,3-CCN-bis-nucleophiles such as anilines and amino-substituted heterocycles with various 1,3-CNC-bis-electrophiles (functionalised isocyanates 17 and isothiocyanates, 18 N-acylated imidoyl chlorides, 19 imidates 20 and imines 21 ) have been recently employed in the synthesis of annulated pyrimidines.…”

“…The structures of compounds 10 and 12 were also established by 1 H, 13 C and 19 F NMR spectroscopy. The most convincing evidence for the formation of the 7-trifluoromethyl-isomer is the chemical shift of C-7 (d C ~65 ppm) with a 2 J CF coupling constant of ~30 Hz.…”

“…According to this explanation, the stable achloro-a,a-diphenylmethyl isocyanate 9 reacted smoothly with a 1,3-thiazole-2,4-diamine salt and 1,2-dimethyl-1Himidazol-5-amine (6) to give thiapurine 11 and purine 13 (Scheme 2, Table 1). The structures of 11 and 13 were established by 13 C NMR spectroscopy, using compounds 10 and 12 as references.…”