Aldimines (generated in situ from aldehydes and amines) react readily with ethyl diazoacetate in the presence of 2 mol% of Bi(OTf) 3 or 5 mol% of Sc(OTf) 3 in [bmim]PF 6 ionic liquid to produce the corresponding aryl aziridine carboxylates in high yields with excellent cis-diastereoselectivity. The recovered ionic liquid containing catalyst was reused in three to four subsequent runs with gradual decrease in activity.
Hydroxy benzothiazepinones were synthesized by a simple procedure involving epoxidation of polymer bound cinnamic acids followed by nucleophilic opening of the resulting glycidic ester by o-aminothiophenol to afford the intermediate hydroxy anilino-esters which underwent cyclization cleavage on heating in DMF to release the product completely.
Aziridine derivatives
Aziridine derivatives R 0040Bi (OTf) 3 -[Bmim]PF 6 : A Novel and Reusable Catalytic System for the Synthesis of cis-Aziridine Carboxylates. -Ionic liquids are successfully used as novel reaction media for the Lewis acid catalyzed highly cis-selective synthesis of aziridines through the three-component coupling reactions of aldehydes, amines and ethyl diazoacetate. The ionic liquid containing the catalyst can be recycled after extraction with diethyl ether and drying under reduced pressure. Optimized results are obtained under conditions A); similar results are observed with 5 mol% Sc(O-Tf) 3 . -(YADAV*, J. S.; REDDY, B. V. S.; REDDY, P. N.; RAO, M. S.; Synthesis 2003, 9, 1387-1390; Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 007, India; Eng.) -Mais 47-101
Aziridine derivativesAziridine derivatives R 0040 LiClO 4 -Catalyzed Highly Diastereoselective Synthesis of cis-Aziridine Carboxylates. -Aldimines, generated in situ from aldehydes (I) and amines (II), undergo ready addition with ethyl diazoacetate (III) in the presence of a catalytic amount of LiClO4 to afford the corresponding cis-aziridines (IV) in high yields and with high diastereoselectivity. -(YADAV*, J. S.; REDDY, B. V. S.; RAO, M. S.; REDDY, P. N.; Tetrahedron Lett. 44 (2003) 28, 5275-5278; Div. Org. Chem., Indian Inst. Chem. Technol., Hyderabad 500 007, India; Eng.) -M. Paetzel 42-101
A diastereoselective, metal-free tandem iodocarbonatecyclization of 1,5-enyne, emulating the reactivity of gold catalysis is described. The normal selectivity of iodonium reagents for alkene is reversed favoring alkyne activation in the presence of aryl alkynes.
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