Journal of the Korean Chemical Society (대한화학회지)

Korean Chemical Society (대한화학회)
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Synthesis of the New Thebaine Derivatives by the Diels-Alder Reaction with Northebaine

Northebaine에 Diels-Alder반응을 이용한 새로운 Thebaine 유도체의 합성

  • Kunjea Kim (Department of Chemistry, Hannam University) ;
  • Kyekwang Kim (Department of Chemistry, Hannam University)
  • 김근재 (한남대학교 이과대학 화학과) ;
  • 김계광 (한남대학교 이과대학 화학과)
  • Published : 1988.08.20
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Abstract

Thebaine was reacted with diisopropyl azodicarboxylate to give northebaine. Diels-Alder reaction between the compound and nitrosobenzene was attempted. The hydrogen of the adducted northebaine was substituted with chloroacetyl chloride and succinic anhydride. We have synthesized the new thebaine derivatives with phenylhydroxylamine at 14-carbon and also acetyl or succinyl at 17-nitrogen with yields of 22% and 16%.

Thebaine과 diisopropyl azodicarboxylate을 반응시켜 northebaine을 합성한 다음 thebaine의 diene에 nitrosobenzene을 dienophile로 하여 Diels-Alder반응을 시도한 후 가수분해하고 succinic anhydride와 chloroacetyl chloride를 각각 반응시켜 14-carbon에 새로운 치환기인 phenylhydroxylamine과 17-nitrogen에 acyl group을 도입한 새로운 화합물(16-A)와 (16-B)를 각각 22와 16%의 수율로 얻었다.

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