Synthesis of Thiochromans via [3+3] Annulation of Aminocyclopropanes with Thiophenols.

Org Lett

Laboratory of Catalysis and Organic Synthesis, Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne, CH-1015 Lausanne, Switzerland.

Published: November 2020

We report the one-pot synthesis of 4-amino thiochromans using simple aminocyclopropanes and thiophenols through a formal [3+3] annulation reaction. This reaction proceeds under mild conditions with good functional group tolerance. The thiochroman core was formed with complete regioselectivity, and modification of complex drug molecules containing an aminocyclopropane was also realized.

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http://dx.doi.org/10.1021/acs.orglett.0c03528DOI Listing

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  • The regioselectivity of the reaction is influenced by the different nucleophilic centers in the benzothiazole structures.
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