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

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 ?-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.

SUBMITTER: Guarnieri-Ibanez A

PROVIDER: S-EPMC5621157 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

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

Guarnieri-Ibáñez Alejandro A Medina Florian F Besnard Céline C Kidd Sarah L SL Spring David R DR Lacour Jérôme J

Chemical science 20170612 8

Using <i>N</i>-sulfonyl triazoles as substrates, compounds as diverse as 2-imino tetrahydrofurans, 13- and 15-membered ring aza-macrocycles can be prepared selectively <i>via</i> 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 ...[more]

PMID: 28989611

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