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Updated: Jun 14, 2025

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines
Published on: January 3, 2018
Two-Step Benzo[e]indole Core Assemblage from Three 1H-1,2,3-Triazole Molecules via "Transannulation/C-H
Ivan V Simdianov1, Pavel A Sakharov1, Alexander F Khlebnikov1
1St. Petersburg State University, Institute of Chemistry, 7/9 Universitetskaya nab., St. Petersburg 199034, Russia.
None:
A two-step synthesis of fluorescent 2,3-dihydrobenzo[e]indole derivatives using only 1H-1,2,3-triazoles as starting materials was developed. At the first step of the synthesis, the 1-alkyl-1,2,3-triazole reacts with two 1-sulfonyl-1,2,3-triazole molecules via the domino transannulation/sulfonamidovinylation sequence under rhodium catalysis. The reaction involving two different 1-sulfonyltriazoles is accomplished in one pot. The further SEAr cyclization of the formed 4-aryl-5-(sulfonamidovinyl)pyrroles using Eaton's reagent provides 2,3-dihydrobenzo[e]indoles having a sulfonylimino-, hydroxy-, and primary amino groups at the C1, C2, and C5 positions, respectively.
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