Synthesis of novel amide derivation of dehydroabietic acid
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POGREBNOI, Vsevolod, STYNGACH, Evgenia, MAKAEV, Fliur. Synthesis of novel amide derivation of dehydroabietic acid. In: Achievements and perspectives of modern chemistry, 9-11 octombrie 2019, Chişinău. Chisinau, Republic of Moldova: Tipografia Academiei de Ştiinţe a Moldovei, 2019, p. 234. 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 novel amide derivation of dehydroabietic acid


Pag. 234-234

Pogrebnoi Vsevolod, Styngach Evgenia, Makaev Fliur
 
Institute of Chemistry
 
 
Disponibil în IBN: 12 noiembrie 2019


Rezumat

The numerous of natural and synthetical substances are represented by isatines and oxindoles. It is known, that the biological activity depends of space structure of chiral compound performing the fundamental role, therefore, the obtaining of active pure enantiomer is a hard challenge. Some reasons when isatines are used as initial compound are accessibility both the original structure with biological activity. We have proposed and realized the synthesis of new compound 4 based on classical reaction of amidation between chloride of natural material – dehydroabietic acid 1 and 5-aminospyrodioxalane 2 followed by deprotection of dioxalane cicle.formulaThe selective extraction from turpentine succeeding by uneasy processes led us to pure [1] dehydroabietic acid 1. Next, it was transformed into chloride by interaction with oxalylchloride in dry chloroform in 5 hours yielded 97%. The famous isatine was used as initial compound in three-stage synthesis of 5-aminospyrodioxalane 2 by two different approaches [2, 3], but the difference in yields varied only 11%. Initially, the compound 3 was synthesized by interaction between 5-aminospyrodioxalane 2 and dehydroabietic acid chloride with equimolar amount of Et3N, but the ultimate deprotecting essay took part in aqueous acetone (1:1) catalyzed by excess of 37% hydrochloric acid leading to enantiomeric pure desired product 4. The target compound was isolated by column chromatography and its structure was proved by NMR.formula