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. 2020 Apr 24;10(27):16101-16109.
doi: 10.1039/d0ra00684j. eCollection 2020 Apr 21.

Ring-opening cyclization of activated spiro-aziridine oxindoles with heteroarenes: a facile synthetic approach to spiro-oxindole-fused pyrroloindolines

Sonal Bhandari  1 , Sravani Sana  1 , Vandana Lahoti  1 , Ramya Tokala  1 , Nagula Shankaraiah  1
Affiliations

Ring-opening cyclization of activated spiro-aziridine oxindoles with heteroarenes: a facile synthetic approach to spiro-oxindole-fused pyrroloindolines

Sonal Bhandari et al. RSC Adv. .

Abstract

Herein, we report a facile tandem approach for the synthesis of both spiro-oxindole-fused pyrroloindolines and benzofurano-pyrrolidines via a Lewis acid-catalyzed domino ring-opening with concomitant ring annulation using activated spiro-aziridines and heteroarenes. This method offers a new class of novel spiro-fused polycyclic pyrrolidines in a one-pot and sustainable manner with good yields and high diastereoselectivity. In addition, the structure of 3d was confirmed by single X-ray crystallography analysis.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. (a) Spiro-oxindole-fused mono and tricyclic pyrrolidine alkaloid natural products and (b) heteroarene-fused tricyclic pyrrolidine natural products.
Scheme 1
Scheme 1. Lewis acid-catalyzed ring-opening of spiro-oxindole aziridines with heteroarenes.
Scheme 2
Scheme 2. Gram-scale reaction.
Scheme 3
Scheme 3. Plausible reaction mechanism.
Fig. 2
Fig. 2. Single X-ray crystal analysis of compound 3d.
Fig. 3
Fig. 3. Optimized B3LYP/6-31G** structures of the reaction; 3D structures represented in cyan color.
See this image and copyright information in PMC

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