Metal- and Solvent-free Synthesis of Functionalized Dihydrooxa­zolo[3,2-a]indoles by One-Pot Tandem Assembly of 3H-Indoles and Propargylic Alcohols

Ludmila A. Oparina; Nikita A. Kolyvanov; Igor A. Ushakov; Anastasiya G. Mal’kina; Alexander V. Vashchenko; Boris A. Trofimov

doi:10.1055/s-0037-1610319

Synthesis, Table of Contents

Synthesis 2019; 51(06): 1445-1454
DOI: 10.1055/s-0037-1610319

paper

Metal- and Solvent-free Synthesis of Functionalized Dihydrooxazolo[3,2-a]indoles by One-Pot Tandem Assembly of 3H-Indoles and Propargylic Alcohols

Ludmila A. Oparina

,

Nikita A. Kolyvanov

,

Igor A. Ushakov

,

Anastasiya G. Mal’kina

,

Alexander V. Vashchenko

,

Boris A. Trofimov*

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russian Federation Email: boris_trofimov@irioch.irk.ru

› Author Affiliations

Abstract

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Abstract

The reaction of 3H-indoles with tertiary propargylic alcohols to give functionalized dihydrooxazolo[3,2-a]indoles in good to excellent yields has been developed. This metal- and solvent-free, one-pot tandem assembly proceeds under mild conditions (22–60 °C) and is regio- and stereoselective: either the Z- or E-isomers (relative to the double bond) are alternatively formed depending on other functionalized substituents on the propargylic alcohols.

Key words

3H-indole - 1H-benzo[e]indole - propargylic alcohols - annulation - dihydrooxazolo[3,2-a]indoles

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References

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Supplementary Material

Supporting Information

Metal- and Solvent-free Synthesis of Functionalized Dihydrooxa­zolo[3,2-a]indoles by One-Pot Tandem Assembly of 3H-Indoles and Propargylic Alcohols

Metal- and Solvent-free Synthesis of Functionalized Dihydrooxazolo[3,2-a]indoles by One-Pot Tandem Assembly of 3H-Indoles and Propargylic Alcohols