Synthesis of some new drimane compounds with 1,3,4-oxadiazole fragment
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ARICU, Aculina; SECARA, Elena; KUCHKOVA, Kaleria; BARBĂ, Alic; DRAGALIN, Ion; UNGUR, Nicon. Synthesis of some new drimane compounds with 1,3,4-oxadiazole fragment. In: Achievements and perspectives of modern chemistry. 9-11 octombrie 2019, Chişinău. Chisinau, Republic of Moldova: Tipografia Academiei de Ştiinţe a Moldovei, 2019, p. 238. 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 some new drimane compounds with 1,3,4-oxadiazole fragment


Pag. 238-238

Aricu Aculina, Secara Elena, Kuchkova Kaleria, Barbă Alic, Dragalin Ion, Ungur Nicon
 
Institute of Chemistry
 
Disponibil în IBN: 12 noiembrie 2019


Rezumat

Many drimane sesquiterpenoids exhibit various biological activity [1]. In continuation of our investigation of the synthesis of nitrogen-containing drimane and homodrimane sesquiterpenoids [2, 3], herein, we describe the synthesis of 5-drimenyl-1,3,4-oxadiazol-2(3H)one (5), 2-amino-5-drimenyl-1,3,4-oxadiazol (6), and 5-drimenyl-1,3,4-oxadiazol-2(3H)-thione (7) from commercially available norambreinolide (1) according to the scheme:formulaReagents and conditions: a) (COCl)2, C6H6, 20°C, 1 h, delta, 1 h; b) N2H4·H2O (98%), CH2Cl2, 20°C, 10 h, 71%; c) CDI, Et3N, THF, 20°C, 20 h, 95%; d) BrCN, NaHCO3, dioxane, 20°C, 12 h, 90%;e) TMTD, DMFA, delta, 1.5 h, 72%.The structures of the newly obtained compounds were proved by IR-, 1H- and 13C NMRspectroscopy, and mass-spectra.