Synthesis 2019; 51(06): 1445-1454
DOI: 10.1055/s-0037-1610319
paper
© Georg Thieme Verlag Stuttgart · New York

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
This work was supported by the Russian Foundation for Basic Research (grant no. 17-03-00927). The main results were obtained with the equipment of Baikal Analytical Center for collective use SB RAS.
Further Information

Publication History

Received: 10 September 2018

Accepted after revision: 18 October 2018

Publication Date:
28 November 2018 (eFirst)

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.

Supporting Information

 
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