Molecular hybridization-guided annulation reactions of isatins with 4-methylpent-3-en-2-one: A direct access to spirooxindole tetrahydropyranones

ABSTRACT

An efficient molecular hybridization strategy has been utilized for the synthesis of pirooxindole tetrahydropyranones 3 through annulation reactions of isatins 1 with 4-methylpent-3-en-2-one 2. Products consist of a pirooxindole tetrahydropyranone scaffold and propan-2-ether unit were smoothly obtained in moderate yields (up to 56% yield). The one-pot, two-step reaction, avoiding the isolation and purification of intermediates C, has proved to be a practical protocol. This protocol leads to new knowledge in the fields of both molecular complexity and the lead compound discovery.

GRAPHICAL ABSTRACT

KEYWORDS:

• 4-Methylpent-3-en-2-one
• annulation reaction
• isatins
• propan-2-ether
• spirooxindole tetrahydropyranone

Additional information

Funding

We are grateful for the financial support from the National Natural Science Foundations of China (No. 81660576, No. 81560563, and No. 81760625); Excellent creative talents of Guizhou province (Qian Jiao He KY Zi [(2015)491] and Qian Ke He Zi [2015]4032, [2017]5609); Project of Guizhou province (Qian Ke He Zi [2016]5623; Qian Ke He LH Zi [2016]7220, [2015]7666, and Qian Ke He Zi [2015]4010) and Major project of the graduate student education teaching reform (Qian Jiao Yan He JG Zi)[2016]06.