초록문의 abstract@kcsnet.or.kr

결제문의 member@kcsnet.or.kr

현재 가능한 작업은 아래와 같습니다.
  • 03월 07일 19시 이후 : 초록수정 불가능, 일정확인 및 검색만 가능

제107회 대한화학회 학술발표회, 총회 및 기기전시회 안내 Studies on Intramolecular Aza-Prins-type Cyclization of Amino Allylsilane

2011년 2월 24일 09시 43분 54초
Ⅳ-ORGN.P-271 이곳을 클릭하시면 발표코드에 대한 설명을 보실 수 있습니다.
금 <발표Ⅳ>
저자 및
손영욱, 이재균1, 배애님2, 이재열, 민선준2, 조용서2
경희대학교 화학과, Korea
1한국과학기술연구원 케모인포매틱스연구단, Korea
2한국과학기술연구원 생체과학연구본부, Korea
The tricyclic benzo[a]quinolizine ring system has been known as a constituent of biologically active natural products and pharmacological molecules. For example, it exists in a type of alkaloids such as berberine, emetine, and tetrabenazine (TBZ), which are known as potential drug candidates for neurological disorders. Although various methods for the construction of these classes of heterocycles are reported, the development of new efficient methods to synthesize such compounds are still challenging to the synthetic organic communities due to their structural novelty and application. Prins cyclization reaction is one of the useful synthetic strategies to construct five- or six- membered ring system containing oxygen or nitrogen heteroatom. In general, this reaction involves the electrophilic addition of alkenes or alkynes to oxonium or iminium intermediates generated from acid-catalyzed condensation of alcohols or amines with carbonyl compounds. Depending on appropriate control of the termination step, feasible functional groups would be introduced to the final cyclized products. In this study, we report an efficient synthesis of benzo[a]quinolizine moiety via aza-Prins-type cyclization of amino allylsilane. Unlike the conventional Prins-type reactions, we found that oxidative C-H activation of isoquinolines by DDQ or PIDA (phenyl iododiacetate) could successfully generate the corresponding iminium species, which underwent cyclization to afford the tricyclic bezoquinoline derivatives in good yields.