Use of Terminally Functionalized Propargyl Silanes for the Synthesis of Various 5-Membered Heterocycles via 1,2-Silyl Migration

Latvijas Universitātes 81. zinātniskā konference. Ķīmijas sekcija 2023
Rasma Kroņkalne, Rūdolfs Beļaunieks, Artjoms Ubaidullajevs, Māris Turks

Small heterocycles, particularly those containing a 5-membered cycle, are popular motifs in pharmaceuticals, displaying a broad range of biological properties. A well-established strategy for the synthesis of 5-membered saturated/partially saturated heterocycles involves intramolecular cyclization, made possible by internal nucleophile attack on carbocations. In this work we investigate the use of electrophile induced 1,2-silyl migration in terminally functionalized propargyl silanes to generate stabilized carbocations, capable of reacting with various internal nucleophiles, forming heterocyclic units. Various nucleophilic species could be utilized, namely alcohols, carboxylic acids, oximes, acyl and sulfonyl amides, carbamates and thioacetates.

Keywords
PROPARGYL SILANES, HETEROCYCLIZATION, 1,2-SILYL MIGRATION
Hyperlink
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Kroņkalne, R., Beļaunieks, R., Ubaidullajevs, A., Turks, M. Use of Terminally Functionalized Propargyl Silanes for the Synthesis of Various 5-Membered Heterocycles via 1,2-Silyl Migration. In: Latvijas Universitātes 81. zinātniskā konference. Ķīmijas sekcija, Latvia, Rīga, 17-17 March, 2023. Rīga: 2023, pp.14-14.

Publication language
English (en)