Isocyanide-Based Multicomponent Bicyclization with Substituted Allenoate and Isatin: Synthesis of Unusual Spirooxindole Containing [5.5]-Fused Heterocycle

Abstract

A three-component bicyclization reaction of isocyanide, substituted allenoate, and isatin has been disclosed. This protocol is proposed to proceed through Michael addition, double cyclization, and [1,5]-hydride shift sequence, thus leading to the formation of two new rings and five new chemical bonds, including C-C, C-O, and C-N bonds.

Isocyanide-Induced Annulation Leading to Cyclopento-, Methano-, and Cyclopentano-[60]Fullerene Derivatives

“…Multicomponent reactions involving alkyl isocyanide and sp-hybridized carbon reactants (i.e., alkynes, allenes) have been widely used to construct cyclic structures in organic synthesis. These reactions are underexplored for the functionalization of fullerenes.…”

A One-Pot Synthesis of Oxazepine-Quinazolinone bis-Heterocyclic Scaffolds via Isocyanide-Based Three-Component Reactions

“…To the best of our knowledge, it is the first report of using two bifunctional starting materials in Ugi reaction to obtain fused oxazepine-quinazolinone heterocycles. Moreover, it is a new isocyanide based bicyclization reaction (Gao et al, 2015, 2016; Hao et al, 2016; Tang et al, 2016). The reaction is high-yielding and product isolation is very straightforward.…”

A Critical Review on Advances in the Multicomponent Synthesis of Pyrroles

“…Another three component, one-pot method for the regio-and stereoselective synthesis of complex spirooxindoles derivatives 142 was investigated by Z. Tang et al, involving the bicyclization of allenoate derivative 141, isatin 140 and isocyanide 139 in toluene at reflexing temperature as shown in Scheme 30. 102 This reaction proceeded through Michael addition, double cyclization, double [1,5]-hydride shift, and nucleophilic addition reaction. Sequence in which two new rings and one C-C, C-O, and C-N bond were formed.…”