Preparation of trifluoromethylpyridine libraries.
S-Alkylation followed by heterocyclization of trifluoromethyl-3-cyano-2(1H)-pyridinethiones was used for preparation of libraries of S-alkyl trifluoromethylpyridines and thieno[2,3-b]pyridines. The S-alkylation (in water--DMF mixtures) was successful for all 18 alkylating agents employed (yields typically > 50%). S-Alkyl derivatives were further converted to corresponding thieno[2,3-b]pyridines via heterocyclization in base conditions (yields > 65%). Structures of new compounds were elucidated by a combination of IR and 1H NMR spectroscopy and elemental analysis and were confirmed by means of single-crystal X-ray diffraction analysis.
Shestopalov
A M
AM
N. D. Zelinsky Institute of Organic Chemistry, Moscow, Russia.
Kislyi
V P
VP
Kruglova EYa
Nikishin
K G
KG
Semenov
V V
VV
Buchanan
A C
AC
Gakh
A A
AA
D004095:Dihydropyridines / Q000138:chemical synthesis; D006540:Herbicides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D009525:Niacin / Q000031:analogs & derivatives / Q000138:chemical synthesis; D011725:Pyridines / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared; D013844:Thiazoles / Q000138:chemical synthesis
D004095:Dihydropyridines; D006540:Herbicides; D011725:Pyridines; D013844:Thiazoles; C407065:trifluoromethylpyridine; D009525:Niacin; C050582:fluazifop; C071869:dithiopyr; C091707:thiazopyr