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Updated: May 21, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
One-Flask, Telescoped Synthesis of Pyrano[3,2-b]indol-2-ones from O-Nitroynones and β-Ketoesters: Further Advancement
K A Sudarshana1,2, Alagesan Balasubramani1,2, Srihari Pabbaraja1,2
1Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
Abstract:
A new general strategy for accessing pyrano[3,2-b]indol-2-ones, a promising fused hybrid heterocyclic system, has been devised from o-nitroynones and β-ketoesters through a one-flask cascade process involving tandem Michael addition, intramolecular cyclization, and Cadogan-Sundberg reductive cyclization. The utility of this approach has been further amplified by leveraging the cycloaddition proclivity of the α-pyrone moiety in pyrano[3,2-b]indol-2-ones toward a concise entry to carbazoles. Illustrative synthesis of the carbazole natural products hyellazole and chlorohyellazole is also disclosed.
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