402929-38-8Relevant articles and documents
Stereoselective syntheses of (E)- and (Z)-2,3-dihydro-3-(1,2,4-triazolyl)-4H-1-benzopyran-4-one oxime ethers
Emami, Saeed,Shafiee, Abbas
, p. 2059 - 2074 (2007/10/03)
A synthesis of (E)-and (Z) -2,3-dihydro-3-(1H-1,2,4-triazol-1-y1)-4H-1-benzopyran-4-one oxime ethers [(E)- and (Z)-13] and (Z)-2,3-dihydro-3-(4H-1,2,4-triazol-4-y1)-4H-1-benzopyran-4-one oxime ethers [(Z)-17] are described. Ring closure of 2-(1,2,4-triazolyl)-2′-hydroxy-acetophenones (5 or 6) followed by reaction with HONH2.HCl gave the corresponding (Z)-oximes [(Z)-11 or (Z)-16]. O-Alkylation of (Z)- oximes afforded (Z)-oxime ethers [(Z)-13 or (Z)-17]. Reaction of (Z)-3-bromo-2,3-dihydro-4H-1-benzopyran-4-one oxime (18) with 1,2,4-triazole afforded (E)-oxime [(E)-11]. O-Alkylation of (E)-oxime gave the desired (E)-oxime ethers [(E)-I3]. In addition, (Z)-oxime ethers [(Z)-13 or (Z)-17)] could also be obtained from the reaction of 2.3-dihydro-3-(1,2,4-triazolyl)-4H-1-benzopyran-4-ones (2 or 14) with O-(arylmethyl)hydroxylamine hydrochloride (19).