Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 559364
Title The stereoselective synthesis of tetrahydrothiopyrano[2,3-b]indole skeletons via tandem reaction of indoline-2-thiones to Baylis-Hillman adduct acetates
Author(s) Moghaddam, Firouz Matloubi; Foroushani, Behzad Koushki; Sobhani, Maryam; Masoud, Nazila; Khodabakhshi, Mohammad Reza; Weng, Ng Seik
Source Tetrahedron 69 (2013)38. - ISSN 0040-4020 - p. 8169 - 8173.
DOI https://doi.org/10.1016/j.tet.2013.07.043
Publication type Refereed Article in a scientific journal
Publication year 2013
Keyword(s) Baylis-Hilman adduct acetates - Indole - Indoline-2-thione - Tandem reaction
Abstract

Indoline-2-thiones (5) were applied as 1,3-dinucleophiles in a tandem reaction with Baylis-Hillman adduct acetates (4) to give novel tetrahydrothiopyrano[2,3-b]indole skeletons (6). The effect of different solvents, bases, and catalysts on the yields and stereochemical outcome was studied in detail. The results indicated that acetonitrile as solvent and K 2CO3 as base, under reflux conditions, were the optimum conditions. Products 6a-6l were obtained in high diastereoselectivity and yield (up to 94%).

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