One-pot multicomponent construction of chromanone-fused pyrrolidinyl spirooxindole collections through a decarboxylative 1,3-dipolar [3 + 2] cycloaddition reaction

Abstract

A new method was developed for the facile one-pot multicomponent construction of heterocycle-fused spiro compounds containing chromanone and pyrrolidinyl spirooxindoles, two potential pharmacophores, in one molecule through a decarboxylative 1,3-dipolar [3 + 2] cycloaddition reaction of carboxylic acid group-activated chromones 1 with isatin-derivated azomethine ylides based on molecular hybridization strategy. A wide variety of products with three contiguous stereocenters including a spiro quaternary stereocenter were smoothly prepared with high efficiency (up to 87% yield and 20:1 diastereomeric ratio). This method could offer libraries of architecturally diverse and multiple pharmacore collections, potentially useful in medicinal chemistry.

GRAPHICAL ABSTRACT

KEYWORDS:

• Decarboxylative
• heterocycle-fused chromanone
• isatin-based azomethine ylides
• pharmacophores
• pyrrolidinyl spirooxindoles

Additional information

Funding

We are grateful for the financial support from the National Natural Science Foundation of China [81760625, 81660576, and 81560563], Guizhou discipline construction project (GNYL[2017]008) and Projects of Guizhou province (Qian Ke He Zi [2015]4001, [2015]4032, [2016]5623, [2017]5609, and JG[2016]06).