6914-23-4Relevant academic research and scientific papers
Montmorillonite clay Cu(II) catalyzed domino one-pot multicomponent synthesis of 3,5-disubstituted isoxazoles
Bharate, Sandip B.,Padala, Anil K.,Dar, Bashir A.,Yadav, Rammohan R.,Singh, Baldev,Vishwakarma, Ram A.
, p. 3558 - 3561 (2013/07/05)
A simple and efficient one-pot multicomponent approach for the synthesis of 3,5-disubstituted isoxazoles directly from corresponding aldehydes and terminal alkynes using recyclable montmorillonite clay supported Cu(II)/NaN3 catalytic system under aqueous conditions have been developed. The 'domino' one-pot MCR approach involves hydroxyamination of aldehydes followed by chlorination and then generation of reactive 'nitrile oxide' which undergoes 1,3-dipolar cycloaddition with alkynes to produce 3,5-disubstituted isoxazoles. The method is operationally simple, regioselective, economical, and possesses excellent functional group compatibility to synthesize structurally diverse isoxazoles in good yields.
Synthesis and reactivity of carbohydroximoyl azides: I. Aliphatic and aromatic carbohydroximoyl azides and 5-substituted 1-hydroxytetrazoles based thereon
Tselinskii,Mel'nikova,Romanova
, p. 430 - 436 (2007/10/03)
Chlorination of 1-hydroxyiminopentane gave 1-chloro-1-nitrosopentane which reacted with sodium azide in DMF to form pentanohydroximoyl azide. The azidation of benzohydroximoyl chlorides was always accompanied by decomposition to benzonitriles. Treatment of carbohydroximoyl azides in ether with gaseous hydrogen chloride afforded 5-butyl-and 5-aryl-1-hydroxytetrazoles which reacted with acetic anhydride to form the corresponding acetates.
