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 SM ISO690:2012ARICU, Aculina, KUCHKOVA, Kaleria, SECARA-KUȘNIR, Elena, BARBA, Alic, DRAGALIN, Ion, VLAD, Pavel. Synthesis of n-(iso-drimenoylamino) carbazole from norambreinolide. In: Ecological and environmental chemistry : - 2017, Ed. 6, 2-3 martie 2017, Chișinău. Chisinau, Republic of Moldova: Academy of Sciences of Moldova, 2017, Ediția 6, pp. 182-183. |
| EXPORT metadate: Google Scholar Crossref CERIF DataCite Dublin Core |
| Ecological and environmental chemistry Ediția 6, 2017 |
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Conferința "Ecological and environmental chemistry 2017" 6, Chișinău, Moldova, 2-3 martie 2017 | ||||||
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| Pag. 182-183 | ||||||
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Many drimane and homodrimane sesquiterpenoids, including those containing nitrogen, are known to exhibit a variety of biological activities [1]. In addition, carbazole derivatives possess antifungal and antitumor activity [2, 3]. The discovery of new biologically active compounds prompted us earlier to synthesize a series of N-containing drimane and homodrimane sesquiterpenoids including 8, 13-bicyclohomofarnesoic acid amides containing pyrimidine and pyrazine rings, which showed significant antimicrobial activity [4]. In continuation of this research we synthesized iso-drimenoic acid amide 10, which incorporate the carbazole ring, in order to combine the biological potential of drimane and carbazole skeletons. Starting drimenoic acid 7 for synthesizing amide 10 was prepared from norambreinolide 1 is known to synthesize from industrial waste of the essential volatile oils production. O O OCOCH3 CH3Li, Et2O P2O5, DMSO OH O CHO OCOCH3 OH CH2Cl2 Et3N CO2H 2 50% H2O2, (CF3CO)2O/NaHCO3 (1:1), CH2Cl2 3 MeSO3SiMe3 (5echiv.), CH3CN 4 5 6 NaClO2, NaH2PO4, t-BuOH, 2-Me-2-butena, H2O 7 1 200C, 15 min. 00C, 10 min, 200C, 30 min, 200C, 10 min. 200C, 40 min. 200C, 2h 10% KOH/MeOH 200C, 1h (65 %) (98 %) (98 %) (95%) (93 %) (94 %) 200C, 40 min. COCl N NH2 CO HN N 8 10 (COCl)2/ C6H6 200C, 1h; , 1h 9 CH2Cl2; 200C, 16 h; , 10h (49 %) OH (95%) Scheme 1 The key steps in the synthesis of drimenoic acid 7 were oxidation of drimenol 5 by P2O5 and DMSO into drimenal 6 and oxidation of drimenal 6 by NaClO2 into drimenoic acid 7. An overall yield of drimenoic acid 7 in the six - steps synthesis is 55%. The reaction of acid 7 with (COCl)2 produced acid chloride 8, reaction of which with N-aminocarbazole 9 formed amide 10 (Scheme 1). The structure of amide 10 was established by IR, 1H – NMR, 13C – NMR, 15N – NMR, and mass – spectral data. It is very likely that acid chloride 8 is formed as a result of the migration of a double bond 7 (8) in acid 7 to 8 (9) in acid chloride 8 in the reaction conditions. The newly synthesized drimane amide 10, containing the carbazole ring is of a scientific and practical importance as compound with a potential biological activity. |
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Cerif XML Export
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The discovery of new biologically active compounds prompted us earlier to synthesize a series of N-containing drimane and homodrimane sesquiterpenoids including 8, 13-bicyclohomofarnesoic acid amides containing pyrimidine and pyrazine rings, which showed significant antimicrobial activity [4]. In continuation of this research we synthesized iso-drimenoic acid amide 10, which incorporate the carbazole ring, in order to combine the biological potential of drimane and carbazole skeletons. Starting drimenoic acid 7 for synthesizing amide 10 was prepared from norambreinolide 1 is known to synthesize from industrial waste of the essential volatile oils production. O O OCOCH3 CH3Li, Et2O P2O5, DMSO OH O CHO OCOCH3 OH CH2Cl2 Et3N CO2H 2 50% H2O2, (CF3CO)2O/NaHCO3 (1:1), CH2Cl2 3 MeSO3SiMe3 (5echiv.), CH3CN 4 5 6 NaClO2, NaH2PO4, t-BuOH, 2-Me-2-butena, H2O 7 1 200C, 15 min. 00C, 10 min, 200C, 30 min, 200C, 10 min. 200C, 40 min. 200C, 2h 10% KOH/MeOH 200C, 1h (65 %) (98 %) (98 %) (95%) (93 %) (94 %) 200C, 40 min. COCl N NH2 CO HN N 8 10 (COCl)2/ C6H6 200C, 1h; , 1h 9 CH2Cl2; 200C, 16 h; , 10h (49 %) OH (95%) Scheme 1 The key steps in the synthesis of drimenoic acid 7 were oxidation of drimenol 5 by P2O5 and DMSO into drimenal 6 and oxidation of drimenal 6 by NaClO2 into drimenoic acid 7. An overall yield of drimenoic acid 7 in the six - steps synthesis is 55%. The reaction of acid 7 with (COCl)2 produced acid chloride 8, reaction of which with N-aminocarbazole 9 formed amide 10 (Scheme 1). The structure of amide 10 was established by IR, 1H – NMR, 13C – NMR, 15N – NMR, and mass – spectral data. It is very likely that acid chloride 8 is formed as a result of the migration of a double bond 7 (8) in acid 7 to 8 (9) in acid chloride 8 in the reaction conditions. 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