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- 저자 : 이창규(Chang Kiu Lee) (검색결과 5 건)
- 무료
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Reactions of Dihydroindole Esters with Bromine: Aromatization vs. Bromination.
이창규(Chang-Kiu Lee),한인섭(In-Sup Han),한인숙(In-Sook Han) 강원대학교 기초과학연구소 1985 기초과학연구 Vol.2 No.-
Dihydroindol Esters와 브롬과의 반응 : 방향족화 대 브롬화 dihydroindole esters의 두 이성질체인 3a,7a-dihydro-(3) 와 2,3- dihydroindole(4) 유도체들의 브롬과의 반응을 연구하였다. 3 은 방향족화가 일어나지만 4 는 두가지의 브롬화 반응 생성물이 된다. 브롬화 화합물의 구조를 분광학적인 방법으로 정립하고 방응상의 차이점을 논의 하였다. Reactions of two ismers of dihydroindole esters,3a,7a-dihydro-(3) and 2,3-dihydroindole(4) derivatives, with bromine are examined. The former gave aromatization while the latter gave two bromination products. The structure of the brominated compounds are established by spectroscopic method and the difference in the reactions are discussed.
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이창규(Chang Kiu Lee),한인섭(In Sup Han) 강원대학교 기초과학연구소 1984 기초과학연구 Vol.1 No.-
Tosyl azide가 2-azabicyclo[2.2.1] hept-5-en-3-one과 반응하여 삽입반응물을 형성하였다. Nitrene 중간체가 반응에 관여하여 C-C이중결함에 첨가반응이 아니라 삽입반응이다. 생성물의 구조는 분광학적인 방법으로 결정하였다. Tosyl azide reacted with 2-azabicyclo[2.2.1] hept-5-en-3-one to give an insertion reaction product. A nitrene intermediate seemed to be involved and the insertion is the prefered mode than addition to C-C double bond. The structure of the product was determined by spectroscopic methods.
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신관석(Kwan Seog Sin),남재우(Jae Woo Nam),이창규(Chang Kiu Lee),전종갑(Jong Gab Jun) 대한약학회 1993 약학회지 Vol.37 No.3
A new series of 7-deazapurine derivatives[7,8] as purine antagonists was prepared. Diethyl 4-cyano-N-(diphenylmethylene)-3-arylglutamate[3] were synthesized by LDA-catalyzed Michael addition of N-(diphenylmethylene)glycine ethyl ester with (E)-2-cyano-3-arylacrylate. Deprotection yields diethyl 4-cyano-3-arylglutamate, which were easily cyclized to 4-cyano-2-ethoxycarbonyl-5-oxo-3-arylpyrrolidine[4]. The compounds[4] were treated with NaBH4 and then with (C2H5)3OBF4 to give 4-cyano-5-ethoxy-2H-2-ethoxymethyl-3-aryl-3,4-dihydropyrrole[6], which were converted to 7-aryl-6-amino-8-ethoxymethyl-7,8-dihydro-7(3H, 9H)-deazapurine-2-thione[7] and 7-aryl-2,6-diamino-8-ethoxymethyl-7,8-dihydro-7(9H)-deazapurine[8] with possible activity against neoplastic disease.
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Aromatization of 3a, 7a-Dihydroindole Ester Derivatives
Lim, Young-Soo,Lee, Chang-Kiu,Hahn, Chi-Sun 연세대학교 자연과학연구소 1985 學術論文集 Vol.15 No.-
3a, 7a-Dihydroindole ester의 N-methyl, N-n-butyl 및 N-benzyl 유도체를 합성하고, 이것들이 methanol 용액중에서 bromine에 의하여 방향족화하는 반응의 메카니즘을 반응속도론적으로 고찰하였다. 여러가지 용매들이 이 반응에서의 생성물의 수율에 미치는 영향과 산화제의 종류가 반응성에 미치는 영향을 살피고 또 산화과정에서의 생성물들을 식별 확인하므로서 소제의 3a, 7a-dihydroindole ester들이 bromine에 의하여 N-bromonium ion intermediate를 형성하고 그 다음 HBr이 제거되는 rate-determining step를 거쳐서 방향족화함을 알 수 있었다. N-Methyl, N-n-butyl and N-benzyl derivatives of 3a, 7a-dihydroindole ester were synthesized, and the kinetics for their aromatization reaction with bromine was studied in methanol solution by UV spectrometry. An intermediate is postulated from the effects of solvents and oxidizing agents on reaction yields, together with an examination of side products. The results indicate that the aromatization occurs by eliminating HBr in the rate-determining step after formation of the N-bromonium ion intermediate.
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Mechanism of Aromatization of 3a, 7a-Dihydroindole Esters
Lim, Young-Soo,Hahn, Chi-Sun,Lee, Chang-Kiu 연세대학교 대학원 1980 延世論叢 Vol.16 No.2
Aromatization of tetramethyl 3a,7a-dihydro-1-alkylindole-2,3,3a,4-tetracarboxylates (2) by bromine was found to be proceeded by the formation of a quartnary N-bromo intermediate at the initial stage of the reaction. The mechanism of the reaction was established by a systematic study of the solvent effect and the measurement of reaction rate. The observed pseudo-first-order rate is consistent with the proposed mechanism. Other oxidizing reagents such as CrO3 or H2O2 were found not to be useful for the aromatization of the dihydroindoles.
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