Synthesis of hydrazide containing trinorlabdane derivatives
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2022-03-18 14:42
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547.597.3:54.057 (1)
Chimie organică (475)
Obținere. Preparare. Izolare. Purificare etc. (51)
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BLAJA, Svetlana, KUCHKOVA, Kaleria, LUNGU, Lidia, LOZOVAN, Vasile, ARICU, Aculina. Synthesis of hydrazide containing trinorlabdane derivatives. In: New frontiers in natural product chemistry.: A destiny on the altar of research. Dedicated to academician Pavel Vlad, Ed. 6, 21 mai 2021, Chișinău. Chișinău, Republica Moldova: Tipografia "Artpoligraf", 2021, Ediția 6, p. 22. ISBN 978-9975-3336-7-2. DOI: https://doi.org/10.19261/nfnpc.2021.ab15
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New frontiers in natural product chemistry.
Ediția 6, 2021
Conferința " New frontiers in natural product chemistry."
6, Chișinău, Moldova, 21 mai 2021

Synthesis of hydrazide containing trinorlabdane derivatives

DOI: https://doi.org/10.19261/nfnpc.2021.ab15
CZU: 547.597.3:54.057

Pag. 22-22

Blaja Svetlana, Kuchkova Kaleria, Lungu Lidia, Lozovan Vasile, Aricu Aculina
 
Institute of Chemistry
 
Proiecte:
 
Disponibil în IBN: 28 mai 2021


Rezumat

The starting material for the synthesis of trinorlabdane compounds with hydrazide fragments was used hydroxyketone (2) which was obtained from commercially available sclareolide (1). Ketone (2) was coupled with 4-phenylthiosemicarbazide in ethanol, to afford compound (3) (Scheme) [1]. Subsequently, instead of obtaining the coordination compound with thiosemicarbazone (3) and Co(II) salt in the presence of hydrogen peroxide, a mixture of two hydrazides (4) and (5) was obtained. Reagents and conditions: a. CH3Li/Et2O, r.t., 15 min., 65%; b. NH2NHCSNHC6H5, EtOH, 6 h, 60°C, 76%; c. CoCl2·6H2O, MeOH, H2O2 30%, r.t., 5 min, (4) 10%, (5) 30%; d. N2H4·H2O, CH3OH, Δ, 10 h, 80%; e. N2H4·H2SO4, MeOH, Δ, 50 min, H2O2 30%, 10 min, 60%. Scheme For this reason, the ketone (2) was treated with N2H4·H2SO4 in methanol, but in this case, only hydrazide (5) was obtained. In another case, hydroxyketone (2) was treated with N2H4·H2O in methanol, giving azine (6) described in [2]. The structure of obtained compounds have been established using modern methods of analysis (ATR-FTIR, 1H, 13C and 15N NMR and GS-MS). The structure and stereochemistry of the compound (4) was confirmed by X-ray diffraction on monocrystal (Figure 1).