126918-27-2Relevant articles and documents
Concise Synthesis of Optically Active Oxirane Precursors for the Preparation of Triazole Antifungals Using the Friedel-Crafts Reaction of (S)-2-Tosyloxypropionyl Chloride
Konosu, Toshiyuki,Tajima, Yawara,Miyaoka, Takeo,Oida, Sadao
, p. 7545 - 7548 (2007/10/02)
Optically active epoxide (2R,3S)-4, a key intermediate for the preparation of triazole antifungal agents (4R,5R)-1 and (2R,3R)-2 (X = 2,4-F2), was synthesized.The Friedel-Crafts reaction between the (S)-lactic acid derivative (S)-10 and m-difluorobenzene gave the (R)-2-chloropropiophenone derivative (R)-11, which was converted into (2R,3R)-18 via Peterson olefination, stereoselective osmium(VIII) oxide oxidation, and mesylation.Treatment of (2R,3R)-18 with sodium triazolide gave (2R,3S)-4.Similarly, the 4-chlorophenyl analog (2R,3S)-4' was prepared.
Triazole derivatives, their preparation and their use as fungicides
-
, (2008/06/13)
Compounds of formula (I): in which: Ar is optionally substituted phenyl; R1 is hydrogen or alkyl; X is optionally unsaturated alkylene, cycloalkylene or both; mis 0 or 1; -Yn-R2 is azido, phthalimido, 1-oxo-2,3-dihydro-2-isoindolyl, protected hydroxy or -OSO2R4 (in which R4 is alkyl group, haloalkyl or optionally substituted phenyl); or Y represents a group of formula -N(R5)CO-, -N(R5)CO-CH=CH-, -O-CO-, -O-CO-CH=CH-, -S-CO- or -S-CO-CH=CH- (in which R5 is hydrogen or alkyl); nis 0 or 1; R2 is alkyl, haloalkyl or optionally substituted phenyl, naphthyl or heterocyclic; and R3 is hydrogen; or R3 and -Xm-Yn-R2 together are a group of formula (II): in which R2 is as defined above, pis 0 or 1, and qis 0 or 1;, and acid addition salts thereof are fungicides, which find considerable value in the eradication of fungi in both agriculture and medicine.