Interrupted Barton–Zard Reaction/Friedel–Crafts Alkylation Telescoped Reaction for the Synthesis of Pyrrolo[3,4‐b]indole Cores

Rešetar, Josip; Remar, Karla; Mikleušević, Ana; Suć Sajko, Josipa; Bašić, Ines; Gredičak, Matija (2025) Interrupted Barton–Zard Reaction/Friedel–Crafts Alkylation Telescoped Reaction for the Synthesis of Pyrrolo[3,4‐b]indole Cores. Asian Journal of Organic Chemistry, 14 (8). ISSN 2193-5807

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Abstract

A dearomatization reaction between electron-deficient indoles and α,α-diaryl-substituted methyleneisocyanides, followed by in situ Friedel–Crafts alkylation, is described. In a telescoped reaction mediated by a Brønsted base in the first step and a Brønsted acid in the second step, aryl-substituted pyrrolo[3,4-b]indole cores are generally obtained in moderate to good yields and with high diastereoselectivity. The reaction tolerates a wide range of 3-nitroindoles and aryl nucleophiles; however, the substrate scope of isocyanide derivatives is limited. The developed methodology offers a modular approach for the synthesis of multi-substituted polycyclic cores.

Item Type:	Article
Uncontrolled Keywords:	Dearomatization; Interrupted Barton–Zard reaction; Friedel–Crafts alkylation; Phase-transfer catalysis; Telescoped reaction
Subjects:	NATURAL SCIENCES NATURAL SCIENCES > Chemistry NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Natural product-inspired organocatalytic dearomatization strategies Matija Gredičak IP-2022-10-5184 istraživački
Depositing User:	Matija Gredičak
Date Deposited:	28 Aug 2025 09:05
URI:	http://fulir.irb.hr/id/eprint/9940
DOI:	10.1002/ajoc.202500261

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