Brønsted Acid-Catalyzed [3 + 2] Cycloaddition of Indoles with Azabicyclobutanes: Access to Indole-Fused 1-Azabicyclo[2.1.1]hexanes.

Authors

Debasis Aich, Arpan Naskar, Subrata Hazra, Suchandrima Banerjee, Boudhayan Bandyopadhyay, Santanu Panda

Published in

Organic letters. Aug 01, 2026. Epub Aug 01, 2026.

Abstract

1-Azabicyclo[2.1.1]hexanes are valuable nitrogen-rich scaffolds with growing importance in medicinal chemistry. We report a Brønsted acid-catalyzed formal cycloaddition of N-substituted indoles with azabicyclobutane (ABB) ketones, providing a mild, transition-metal-free, and highly stereoselective route to aza-bicyclohexanes. Using pTSA·H2O in HFIP, the reaction proceeds at room temperature in up to 93% yield and 99:1 d.r. Mechanistic studies suggest cooperative activation by pTSA and HFIP via hydrogen-bond-assisted proton transfer. The synthesized scaffolds also exhibited promising antimicrobial activity.

PMID:
42542965
Bibliographic data and abstract were imported from PubMed on 02 Aug 2026.

Read full publication at:
Please sign in to see all details.

Stats

1-terrible, 9-excellent. How would you rate this publication? Sign in in to submit your rating.

Post a comment

You need to be signed in to post comments. You can sign in here.

Comments

There are no comments yet.