title: Direct alkenylation of indolin-2-ones by 6-aryl-4-methylthio-2H-pyran-2-one-3-carbonitriles: a novel approach.
abstract: A direct one-pot base-induced alkenylation of indolin-2-ones has been developed by using 6-aryl-4-methylthio-2H-pyran-2-one-3-carbonitriles. Different bases such as MeONa, NaH and t-BuONa have been used to optimize the reaction conditions to obtain the desired product. NaH in THF was found to be the most suitable for the alkenylation of indolin-2-ones. Reaction in the presence of other bases led to the formation of 1-aryl-3-methoxy/methylthio-5H-dibenzo[d,f][1,3]diazepin-6(7H)-ones. Quantum chemical calculations have been performed to explain the nature of the weak noncovalent interactions operating in the supramolecular architectures of alkenylated indoline-2-ones and to explain the relative stability of one of the tautomers with respect to the others.
authors.affiliation: Department of Chemistry, University of Lucknow, Lucknow-226007, India.
authors.forename: Sandeep
authors.initials: S
authors.lastname: Kumar
authors.forename: Ramendra
authors.initials: R
authors.lastname: Pratap
authors.forename: Abhinav
authors.initials: A
authors.lastname: Kumar
authors.forename: Brijesh
authors.initials: B
authors.lastname: Kumar
authors.forename: Vishnu K
authors.initials: VK
authors.lastname: Tandon
authors.forename: Vishnu Ji
authors.initials: VJ
authors.lastname: Ram
keywords: 2H-pyran-2-one; alkenylation; dibenzo[d,f][1,3]diazepin-6(7H)-one; indolin-2-one; ketene dithioacetal