Synthesis of some new homodrimane sesquiterpenoids with 1,3,4-oxadiazole fragment
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ARICU, Aculina; KUCHKOVA, Kaleria; SECARA, Elena; BARBA, Alic; DRAGALIN, Ion; UNGUR, Nicon. Synthesis of some new homodrimane sesquiterpenoids 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. 239. 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 homodrimane sesquiterpenoids with 1,3,4-oxadiazole fragment


Pag. 239-239

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


Rezumat

For the purpose searching of new biologically active compounds, herein, we describe the obtaining of 5-(delta8,9-bicyclohomofarnesenyl)-1,3,4-oxadiazol-2(3H)-thione (5), 2-allylamino-5-(delta8,9-bicyclohomofarnesenyl)-1,3,4-oxadiazole (7a), and 2-phenylamino-5-(delta8,9bicyclohomofarnesenyl)-1,3,4-oxadiazole (7b) from commercially available norambreinolide (1), according the scheme.formulaReagents and conditions: a) (COCl)2, C6H6, 20°C, 1 h, delta, 1 h; b) N2H4•H2O (98%), CH2Cl2, 20°C, 2 h, delta, 6 h, 65%; c) TMTD, DMF, 90°C, 1.5 h, 70%; d) R-NCS, EtOH, 20°C, 4 h, 8090%; e) DCC, CH3OH – CH3COCH3 (1:1), delta, 5 h, 56-76%. The structures of the newly obtained compounds were proved by IR-, 1H- and 13C NMRspectroscopy and mass-spectra.

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<title xml:lang='en'><p>Synthesis of some new homodrimane sesquiterpenoids with 1,3,4-oxadiazole fragment</p></title>
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<description xml:lang='en' descriptionType='Abstract'><p>For the purpose searching of new biologically active compounds, herein, we describe the obtaining of 5-(delta8,9-bicyclohomofarnesenyl)-1,3,4-oxadiazol-2(3H)-thione (5), 2-allylamino-5-(delta8,9-bicyclohomofarnesenyl)-1,3,4-oxadiazole (7a), and 2-phenylamino-5-(delta8,9bicyclohomofarnesenyl)-1,3,4-oxadiazole (7b) from commercially available norambreinolide (1), according the scheme.</p><p>formula</p><p>Reagents and conditions: a) (COCl)2, C6H6, 20&deg;C, 1 h, delta, 1 h; b) N2H4&bull;H2O (98%), CH2Cl2, 20&deg;C, 2 h, delta, 6 h, 65%; c) TMTD, DMF, 90&deg;C, 1.5 h, 70%; d) R-NCS, EtOH, 20&deg;C, 4 h, 8090%; e) DCC, CH3OH &ndash; CH3COCH3 (1:1), delta, 5 h, 56-76%. The structures of the newly obtained compounds were proved by IR-, 1H- and 13C NMRspectroscopy and mass-spectra.</p></description>
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