Treatment of 1-chloromethylbenzotriazole (4) with salicylonitrile (5a), thiosalicylonitrile (5b), ethyl N-(2-cyanophenyl)carbamate (5c), and N-(2-cyanophenyl)methane-sulfonamide (5d) provided the corresponding intermediates 3. Cyclization of compounds 3a-3c with LDA gave 2- (2c), respectively. Attempts to accomplish elimination of the benzotriazole nitrogen under both thermal and photolytic conditions failed.

A new synthesis of latanoprost diastereoisomers is described which utilizes a highly stereoselective Michael addition of higher-order cuprate to a chiral cyclopentenone derived from G-lactone in the crucial skeleton-forming step.

Two synthetic approaches to the achiral quinoline fragment of simeprevir are described. Both approaches are based on the synthesis of methyl 4-hydroxy-7-methoxy-8-methylquinoline-2carboxylate, protection of its 4-hydroxyl group, and construction of the thiazole ring from the ester group at the 2-position. The last step is acid deprotection of the 4-hydroxyl protecting group.

Synthesis of 3-unsubstituted 1-alkyl- and 1-aryl-1,4-dihydroquinolin-4-ones from 2-nitroacetophenone via the corresponding 3-amino-1-(2-nitrophenyl)prop-2-en-1-ones and -but-2-en-1-ones by denitrocyclization reaction is described. The nucleophilic cyclization was achieved either by sodium hydride or potassium carbonate in DMF.

Synthesis. -Two different approaches to the title compound which is a building block of the drug candidate simeprevir with specific HCV protease inhibitory activity are described. Both syntheses proceed via methyl 4,7-dimethoxy-8-methylquinoline-2-carboxylate the preparation of which from the corresponding aniline is elaborated. -(RADL*, S.; REZKOVA, H.; OBADALOVA, I.; SRBEK, J.; BRICHAC, J.; PEKAREK, T.; Synthesis 46 (2014) 7, 899-908, http://dx.