Synthesis of 1,2,3-triazoles from (1r,3r,4r,6s)-4-azido-4,7,7-trimethylbicyclo [4.1.0]heptan-3-ole

Curlat Serghei; Barba Alic; Makaev Fliur

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2023-06-26 12:01

SM ISO690:2012

CURLAT, Serghei, BARBA, Alic, MAKAEV, Fliur. Synthesis of 1,2,3-triazoles from (1r,3r,4r,6s)-4-azido-4,7,7-trimethylbicyclo [4.1.0]heptan-3-ole. In: Achievements and perspectives of modern chemistry, 9-11 octombrie 2019, Chişinău. Chisinau, Republic of Moldova: Tipografia Academiei de Ştiinţe a Moldovei, 2019, p. 215. ISBN 978-9975-62-428-2.

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Achievements and perspectives of modern chemistry 2019

Conferința "International Conference "Achievements and perspectives of modern chemistry""
Chişinău, Moldova, 9-11 octombrie 2019

Synthesis of 1,2,3-triazoles from (1r,3r,4r,6s)-4-azido-4,7,7-trimethylbicyclo [4.1.0]heptan-3-ole

Pag. 215-215

Curlat Serghei, Barba Alic, Makaev Fliur

Institute of Chemistry

Disponibil în IBN: 11 noiembrie 2019

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Since Huisgen dicovery of the use of Cu (I) salts as catalyst in reactions of 1,4-substituted 1,2,3-triazoles construction by cycloaddition of azides and terminal alkynes, this ddirection has been widely developed in organic chemistry. In present, a large number of Cu(I) complexes have been proposed as catalysts for this reaction. Our intention was to prepare 1,2,3-triazoles functionalized (1R,3R,4R,6S)-4,7,7trimethylbicyclo[4.1.0]heptan-3-oles from bicyclic monoterpene(+)-3-carene 1 via initial formation of epoxide 2 with a system a-Al2O3/H2O2[1]. Transformation of 2 to azidoalcohol 3 was confirmed by independent experiments, where aqueous acetic acid solution of it was treated with sodium azide [2].formulaWe have studied reactions of azidoalcohol 3 with substituted alkynes aimed on developing synthetic approaches to potentially bioactive polysubstituted 1,2,3-triazoles structures. Treatment of optically active azidoalcohol 3 with monosubstituted alkynes utilizing the CuI/DIPEA or (CuSO4/ sodium ascorbate) under mild reaction conditions afforded the corresponding enatiomeric pure 1,2,3-triazoles functionalized (1R,3R,4R,6S)-4,7,7trimethylbicyclo[4.1.0]heptan-3-oles 4a-4f in good yields.

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