One-Flask, Telescoped Synthesis of Pyrano[3,2-b]indol-2-ones from O-Nitroynones and β-Ketoesters: Further Advancement to Functionalized Carbazoles

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 19, 2025

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 one-flask cascade process involving tandem Michael addition, intramolecular cyclization, Cadogan-Sundberg reductive cyclization. The utility of this approach further amplified by leveraging the cycloaddition proclivity α-pyrone moiety in pyrano[3,2-b]indol-2-ones toward concise entry to carbazoles. Illustrative synthesis carbazole natural products hyellazole chlorohyellazole is also disclosed.

Language: Английский

Synthesis of dithioacetals via nucleophilic substitution and their antifungal activity evaluation

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A novel substitution reaction of dichloromethane with thiols is developed, affording varieties dithioacetals and α-acyloxy sulfides in up to 96% yields. Moreover, the obtained exhibit excellent antifungal activity against L. theobromae .

Language: Английский