Facile stereoslective synthesis of spiro[indole-oxiranes] by combination of phase transfer catalyst and ultrasound irradiation and their bioassay
摘要:
An alternative and environmentally benign pathway for diastereoslective synthesis of fluorinated spiro[indole-3,2'-oxirane]-3'-benzoyl-2(1H)-ones (2a-g) is reported. The spiro[indole-3.2'-oxiranes] derivatives were obtained in 90-97% yield exclusively via the epoxidation of 3-aroylmethylene indole-2-ones with 30% aqueous hydrogen peroxide using cetyltrimethyl ammonium bromide as a phase transfer catalyst under ultrasound irradiation. The lead compounds have been tested for their antimicrobial activity and antioxidant properties. (C) 2010 Elsevier B.V. All rights reserved.
A mild and efficient reaction of the Bestmann–Ohirareagent with N-unprotected isatin-derived olefins has been developed for the selective synthesis of spiro-pyrazoline-oxindoles and tricyclic pyrazoles. The reaction features an attractive product-selectivity depending on the substituent on isatin-derived olefin. Treatment of 3-aryl/alkylideneoxindoles with BOR afforded spiropyrazoline-oxindoles, whereas