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Sydnone 유도체들의 diazo coupling 반응에 관한 연구
안찬묵 연세대학교 대학원 1991 延世論叢 Vol.27 No.1
Diazo couplings at 3- or 4-phenyl ring of sydnone is described. First, nitration of 3,4-diphenylsydnone was examined under various conditions. It was found that the reaction took place only at the 4-phenyl ring of sydnone. Under CH3COOH-HNO3 conditions the parasubstitiuent was obtained, whereas the ortho- and para-substitiuent was obtained under H2SO4 -HNO3 conditions. The para-substituted compound was reduced with Fe and 2% aqueous CH3 COOH to give 3-phenyl- (4'-aminophenyl)sydnone. Diazo coupling with these amino compound in acidic conditions was tried, but the reaction did not proceed. Next, diazo coupling of 3 - phenylsydnone was examined. In order to obtain a compound which has an amino group at 3 - phenol ring, 3- (p-nitrophenyl)sydnone was reduced with Fe and 2% aqueous CH3COOH to give 3- (p-aminophenyl)sydnone. This amino compound was treated with sodium nitrite in acidic conditions, and then reacted with various reagents(I-VIII)to give auto compounds.
Selective Nitration에 의한 3-Phenyl-4-(p-aminophenyl) Sydnone의 합성
안찬묵,윤병희,유학수 연세대학교 자연과학연구소 1986 學術論文集 Vol.16 No.-
3,4-Diphenylsydnone에 조건을 변화시켜가면서 니트로화반응을 시켰다. 반응은 4위치의 phenyl에서만 일어났으며, CH_3COOH-HNO_3조건하에서는 para에 그리고 H_2SO_4-HNO_3조건하에서는 ortho와 para에 진행하여 각각 니트로화합물을 얻었다. 생물학적으로 활성을 갖을 것으로 기대되는 아미노기를 갖는 sydnone유도체를 얻기 위하여, 이 니트로화합물을 Fe와 2%초산수용액에 의해 환원시켰다. 이들 생성물의 확인은 IR과 NMR로 검토하였으며 원소분석으로 확정지었다. Nitration of 3,4-diphenylsydnone was examined under various conditions. Reaction took place only at phenyl which was at 4-position of sydnone ring, and it was found that para-substituent was obtained under CH_3COOH-HNO_3 condition, whereas under H_2SO_4-HNO_3 condition ortho-and para-substituent was obtained. In order to obtain amino group containing sydnone derivative which was expected to be biologically active, this nitro compound was reduced by iron and 2% aqueous acetic acid. The products thus obtained were identified by IR and NMR spectroscopy and confirmed by elemental analysis.
안찬묵,우호범,Ahn Chan Mug,Ho Bum Woo 대한화학회 2003 대한화학회지 Vol.47 No.4
A strategy for synthesis of the furan-fused tetracyclic system of xestoquinone was explored through a model study. Using 3-butyn-1-ol as a starting material, 5-iodo-1-methoxymethoxy pentyne (5) was prepared in 5 steps. Reaction of ethyl 2-phenylpropanoate with 5 gave ethyl 7-methoxymethoxy-2-methyl-2-phenyl-5-heptynoate (6) in 88% yield, and then methyl 9-oxo-4-methyl-4-phenyl-2,7-nonadiynoate (13), the key intermediate, was synthesized in 6 steps from the ester 6. Intramolecular cycloaddition reaction of 13 afforded isobenzofuran 14 in 5% yield, which was converted to the tetracyclic structure 15 in the presence of Lewis acid. Xestoquinone의 퓨란-접합된 4환계화합물에 대한 합성전략을 모델연구를 통하여 조사하였다. 출발물질로서 3-butyn-1-ol을 이용하여, 5-iodo-1-methoxymethoxypentyne(5)이 5단계를 거쳐 제조되었다. Ethyl 2-phenylpropanoate와 5의 반응으로부터 ethyl 7-methoxymethoxy-2-methyl-2-phenyl-5-heptynoate(6)가 88%의 수득율로 얻어졌으며, 6으로부터 중요한 중간체인 methyl 9-oxo-4-methyl-4-phenyl-2,7-nonadiynoate(13)가 6단계를 거쳐 합성되었다. 13의 분자내 고리화반응은 5%의 수득율로 isobenzofuran 14을 생성하였으며, Lewis acid 존재 하에서 4환고리 구조로 전환되었다.
Penta-2, 3-dibromopropoxychlorocyclotriphos- phazene의 합성과 그의 방염성에 관한 연구
채희주,안찬묵,고석원,Chae, Hui-Ju,An, Chan-Muk,Go, Seok-Won 한국섬유공학회 1984 한국섬유공학회지 Vol.21 No.3
Penta-2,3-dibromopropoxychlorocyclotriphosphazene, N3P3Cl(OCH2CHBrCH2Br)5, 〔III〕, contains phosphorus, nitrogen and bromine which are reported to react with cellulose to give durable flame retardant properties. This model compound III was synthesized by the following methods and identified. Hexachlorocyclotriphosphazene and 2, 3-dibromopropanol was refluxed in benzene solvent catalysed by pyridine for 60 hrs and purified by vacuum distillation and by liquid chromatography. This compound III was identified by IR, mass, GC and elemental analysis of C,H,N and halogens. This compound III reacts with cotton through a condensation reaction to make a durable chemical bonding by interaction of P-Cl bond and OH group of cellulose. This was identified by study of IR and modified combustion method and by comparing its thermal behavior by TGA and DSC analysis with that of untreated cotton. Finished cotton fabric showed a notable flame retardant properties as limited oxygen index was 0.275 in contrast with 0.175 for untreated cotton fabric.