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Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes

Published inChemical science, vol. 8, no. 8, p. 5713-5720
Publication date2017
Abstract

Using N-sulfonyl triazoles as substrates, compounds as diverse as 2-imino tetrahydrofurans, 13- and 15-membered ring aza-macrocycles can be prepared selectively via formal [1 + 4], [5 + 4 + 4] and [3 + 4 + 4 + 4] condensations of α-imino carbenes and oxetanes under Rh(II)-catalysis or thermal activation. Spirocyclic N-heterocycles are also accessible by means of Buchwald–Hartwig and Pictet–Spengler cyclizations. By reaction control, substrate selection or further derivatization, a large variety of chemical structures is thus achievable. Finally, using triazoles reacting under thermal activation, interesting mechanistic insight was obtained.

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Citation (ISO format)
GUARNIERI IBANEZ, Alejandro José et al. Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes. In: Chemical science, 2017, vol. 8, n° 8, p. 5713–5720. doi: 10.1039/C7SC00964J
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ISSN of the journal2041-6520
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Creation07/25/2017 11:03:00 AM
First validation07/25/2017 11:03:00 AM
Update time03/15/2023 1:51:18 AM
Status update03/15/2023 1:51:18 AM
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