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CC BY-NC-ND 4.0 · SynOpen 2022; 06(01): 7-10
DOI: 10.1055/s-0040-1719868
paper
Virtual Collection in Honor of Prof. Issa Yavari

Synthesis of [1,4]Oxathiepino[5,6-b]quinolines via Base-Mediated Intramolecular Hydroalkoxylation

Maryam-Sadat Tonekaboni
a   Department of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Tehran, Iran
,
Zahra Tanbakouchian
a   Department of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Tehran, Iran
,
Soma Majedi 
b   Medical Analysis Department, Faculty of Science, Tishk International University, Erbil, Kurdistan Region, Iraq
,
Morteza Shiri  ∗
a   Department of Chemistry, Faculty of Physics and Chemistry, Alzahra University, Tehran, Iran
› Author AffiliationsWe are thankful to Alzahra University and the Iran National Science Foundation (INSF) for financial support.
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This paper is dedicated to Prof. Issa Yavari.

Abstract

A base-mediated intramolecular hydroalkoxylation that was used to prepare a series of seven-membered S,O-heterocycles is described. 2-Thiopropargyl-3-hydroxymethyl quinolines were prepared starting from 2-mercaptoquinoline-3-carbaldehydes, via S-propargylation and reduction of a formyl group. Interestingly, 2-mercaptopropargyl-3-hydroxymethyl quinolines were converted into the corresponding oxathiepinoquinolines in the presence of t-BuOK. It is proposed that the S-propargyl moiety, in the presence of base, is converted into its allenyl isomer; subsequent addition of a hydroxyl group to the terminal double bond yields the 3-methyl-5H-[1,4]oxathiepino[5,6-b]quinoline in good to high yield. Notably, the procedure is adaptable to the conversion of N-propargyl indole-2-methanol into the corresponding intramolecular hydroalkoxylation product.

Key words

quinoline - 2-chloroquinoline-3-carbaldehyde - intramolecular reactions - hydroalkoxylation - base-mediated cyclization - allenes

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1719868.
  • Supporting Information


Publication History

Received: 24 September 2021

Accepted after revision: 20 December 2021

Article published online:
10 January 2022

© 2022. This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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