메뉴 건너뛰기




Volumn , Issue 8, 1999, Pages 1349-1353

A divergent method for preparing 1-aryl- and 1,3-diarylazulenes from ethyl 3-(cyclohepta-1,3,5-trien-1-yl)-3-oxopropionate

Author keywords

Azulenes; Azulenones; Dehydrogenation; Nazarov cyclization

Indexed keywords

1,2,3,8 TETRAHYDROAZULEN 1 ONE; 3 (CYANOHEPTA 1,3,5 TRIEN 1 YL) 3 OXOPROPIONIC ACID ETHYL ESTER; ALDEHYDE; AZULENE DERIVATIVE; CYCLOHEPTANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0032871009     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3546     Document Type: Article
Times cited : (25)

References (38)
  • 5
    • 84985516536 scopus 로고
    • a) Scott, L. T.; Brunsvold, W. R.; Kirms, M. A.; Erden, I. Angew. Chem. 1981, 93, 282; Angew. Chem., Int. Ed. Engl. 1981, 20, 284.
    • (1981) Angew. Chem., Int. Ed. Engl. , vol.20 , pp. 284
  • 14
    • 0000646877 scopus 로고
    • Trost, B. M.; Fleming, I. Ed.; Pergamon; Oxford; ch. 6.3
    • b) Denmark, S. Comprehensive Organic Synthesis, Vol. 5, Trost, B. M.; Fleming, I. Ed.; Pergamon; Oxford, 1991; ch. 6.3, p 751.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 751
    • Denmark, S.1
  • 24
    • 0000248247 scopus 로고
    • Wiley: New York
    • a) Jones, G. Organic Reactions, Vol. 15; Wiley: New York, 1967; p 204.
    • (1967) Organic Reactions , vol.15 , pp. 204
    • Jones, G.1
  • 25
    • 0000201762 scopus 로고
    • Trost, B. M.; Fleming, I. Ed.; Pergamon: Oxford; ch. 1.11
    • b) Tietze, F. L.; Beifuss, U. Comprehensive Organic Synthesis, Vol. 2, Trost, B. M.; Fleming, I. Ed.; Pergamon: Oxford, 1991; ch. 1.11, p 341.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 341
    • Tietze, F.L.1    Beifuss, U.2
  • 26
    • 0344263767 scopus 로고    scopus 로고
    • note
    • The stereochemical relationship between the ester and aryl groups in 7 was determined to be trans, as seen in the other derivatives (see, ref 6). Similar results were reported in the Knoevenagel condensation of ethyl 3-oxo-3-phenylpropionate with benzaldehyde, though the reaction of methyl acetoacetate was known to give a mixture of geometrical isomers; see following references and those cited therein.
  • 29
    • 85086352294 scopus 로고    scopus 로고
    • note
    • vic between the protons at the 2 and 3 positions of 2c is 2.8 Hz, suggesting a trans-arrangement. See ref 6 and the following references.
  • 34
    • 0000478319 scopus 로고
    • Wiley: New York
    • Shapiro, R. H. Organic Reactions, Vol. 23; Wiley: New York, 1976; p 405.
    • (1976) Organic Reactions , vol.23 , pp. 405
    • Shapiro, R.H.1
  • 36
    • 0141551101 scopus 로고
    • We have already reported that a thermolytic method with Pd-C in refluxing diphenyl ether is effective to prepare some azulene derivatives, see: Kuroda, S.; Hirooka, S.; Iwaki, H.; Ikeda, M.; Nakao, T. Ogisu, M. Yasunami, M.; Takase, K. Chem. Lett. 1986, 2039. Kuroda S.; Hirooka, S.; Oda, M.; Iwaki, H.; Teranishi, S.; Matsushita, N.; Hongou, T.; Ikeda, M.; Hayashi, S.; Miyatake, R.; Izawa, M.; Yamada, M.; Shimao, I. Bull. Chem. Soc. Jpn. 1998, 71, 459.
    • (1986) Chem. Lett. , pp. 2039
    • Kuroda, S.1    Hirooka, S.2    Iwaki, H.3    Ikeda, M.4    Nakao, T.5    Ogisu, M.6    Yasunami, M.7    Takase, K.8
  • 38
    • 0000829582 scopus 로고
    • Houben-Weyl; Carbocyclische p-Elektronen-Systeme Kropf, H. Ed.; Thieme: Stuttgart
    • Zeller, K.-P. Methoden Der Organischen Chemie (Houben-Weyl), Bd. 5, 2c; Carbocyclische p-Elektronen-Systeme Kropf, H. Ed.; Thieme: Stuttgart, 1985; p. 127.
    • (1985) Methoden Der Organischen Chemie , vol.5 , Issue.2 C , pp. 127
    • Zeller, K.-P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.