Scalable Synthesis of Seven-Membered 3,4-Fused Tricyclic Indole Scaffolds Enabling Conformationally Fixed Aminobenzosuberene Analogues

Scalable Synthesis of Seven-Membered 3,4-Fused Tricyclic Indole Scaffolds Enabling Conformationally Fixed Aminobenzosuberene Analogues Full article

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2026, Volume: 91, Number: 22, Pages: 7464–7470 Pages count : DOI: 10.1021/acs.joc.6c00478

Authors

Adaeva Olga I. ¹ , Demchuk Dmitry V. ¹ , Semenova Marina N. ¹ , Semenov Victor V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation

We report an improved and scalable synthetic route to seven-membered 3,4-fused tricyclic indole scaffolds, providing practical access to the target framework with good overall efficiency and reproducibility. A key feature is Sc(OTf)3-promoted regioselective Fischer indolization of ortho-substituted phenylhydrazone 5b, which overrides the anomalous pathway observed under conventional acidic conditions. The synthetic utility of the scaffold was demonstrated through the preparation of aminobenzosuberene-inspired derivatives. Preliminary biological evaluation revealed that compound 1b exhibited antimitotic activity at 0.2 μM.

Adaeva O.I. , Demchuk D.V. , Semenova M.N. , Semenov V.V.
Scalable Synthesis of Seven-Membered 3,4-Fused Tricyclic Indole Scaffolds Enabling Conformationally Fixed Aminobenzosuberene Analogues
Journal of Organic Chemistry. 2026. V.91. N22. P.7464–7470. DOI: 10.1021/acs.joc.6c00478 WOS Scopus OpenAlex

Submitted:	Feb 25, 2026
Published online:	Jun 5, 2026

≡ Web of science:	WOS:001770314100001
≡ Scopus:	2-s2.0-105040927290
≡ OpenAlex:	W7161724170