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Volumn 64, Issue 17, 1999, Pages 6499-6504

Pyrylium salts via electrophilic cyclization: Applications for novel 3- arylisoquinoline syntheses

Author keywords

[No Author keywords available]

Indexed keywords

INORGANIC SALT; PYRYLIUM DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033588393     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990810x     Document Type: Article
Times cited : (103)

References (28)
  • 1
    • 0000045323 scopus 로고
    • Foerst, W., Ed. Academic Press: New York
    • For some leading reviews, see: (a) Dimroth, K.; Wolf, K. H. In Newer Methods of Preparative Organic Chemistry; Foerst, W., Ed. Academic Press: New York, 1964; Vol. 3, pp 357-423. (b) Balaban, A. T.; Schroth, W.; Fischer, G. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: New York, 1969; Vol. 10, pp 241-326. (c) Balaban, A. T.; Dinculescu, A.; Dorofeenko, G. N.; Fischer, G. W.; Koblik, A. V.; Mezheritskii, V. V.; Schroth, W. Pyrylium Salts: Syntheses, Reactions, and Physical Properties; Academic Press: New York, 1982.
    • (1964) Newer Methods of Preparative Organic Chemistry , vol.3 , pp. 357-423
    • Dimroth, K.1    Wolf, K.H.2
  • 2
    • 33845347239 scopus 로고
    • Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: New York
    • For some leading reviews, see: (a) Dimroth, K.; Wolf, K. H. In Newer Methods of Preparative Organic Chemistry; Foerst, W., Ed. Academic Press: New York, 1964; Vol. 3, pp 357-423. (b) Balaban, A. T.; Schroth, W.; Fischer, G. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: New York, 1969; Vol. 10, pp 241-326. (c) Balaban, A. T.; Dinculescu, A.; Dorofeenko, G. N.; Fischer, G. W.; Koblik, A. V.; Mezheritskii, V. V.; Schroth, W. Pyrylium Salts: Syntheses, Reactions, and Physical Properties; Academic Press: New York, 1982.
    • (1969) Advances in Heterocyclic Chemistry , vol.10 , pp. 241-326
    • Balaban, A.T.1    Schroth, W.2    Fischer, G.3
  • 7
    • 0344130627 scopus 로고
    • For representative synthetic strategies, see: (a) Bradsher, C. K.; Wallis, T. G. Tetrahedron Lett. 1972, 3149-3150. (b) Garcia, A.; Lete, E.; Villa, M. J.; Dominguez, E.; Badia, M. D. Tetrahedron 1988, 44, 6681-6686. (c) Fitzgerald, J. J.; Michael, F. E.; Olofson, R. A. Tetrahedron Lett. 1994, 35, 9191-9194.
    • (1972) Tetrahedron Lett. , pp. 3149-3150
    • Bradsher, C.K.1    Wallis, T.G.2
  • 8
    • 0001467516 scopus 로고
    • For representative synthetic strategies, see: (a) Bradsher, C. K.; Wallis, T. G. Tetrahedron Lett. 1972, 3149-3150. (b) Garcia, A.; Lete, E.; Villa, M. J.; Dominguez, E.; Badia, M. D. Tetrahedron 1988, 44, 6681-6686. (c) Fitzgerald, J. J.; Michael, F. E.; Olofson, R. A. Tetrahedron Lett. 1994, 35, 9191-9194.
    • (1988) Tetrahedron , vol.44 , pp. 6681-6686
    • Garcia, A.1    Lete, E.2    Villa, M.J.3    Dominguez, E.4    Badia, M.D.5
  • 9
    • 0028077171 scopus 로고
    • For representative synthetic strategies, see: (a) Bradsher, C. K.; Wallis, T. G. Tetrahedron Lett. 1972, 3149-3150. (b) Garcia, A.; Lete, E.; Villa, M. J.; Dominguez, E.; Badia, M. D. Tetrahedron 1988, 44, 6681-6686. (c) Fitzgerald, J. J.; Michael, F. E.; Olofson, R. A. Tetrahedron Lett. 1994, 35, 9191-9194.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 9191-9194
    • Fitzgerald, J.J.1    Michael, F.E.2    Olofson, R.A.3
  • 13
    • 0345424305 scopus 로고    scopus 로고
    • note
    • Disappearance of the decyloxy group's α-proton triplet (4.18 ppm) led us to this conclusion.
  • 14
    • 0345424304 scopus 로고    scopus 로고
    • note
    • --promoted TMS cleavage.
  • 17
    • 0345424301 scopus 로고    scopus 로고
    • note
    • Please see the Supporting Information for complete experimental and structural data.
  • 19
    • 0033015987 scopus 로고    scopus 로고
    • During preparation of this manuscript, we found a recently published procedure which effected cyclizations of o-ethynylpyridinecarbaldehydes to the corresponding naphthyridines upon exposure to ethanolic ammonia at 80°C in a sealed tube: Numata, A.; Kondo, Y.; Sakamoto, T. Synthesis 1999, 306-311. Applying this protocol to 2k gave a 37% crude yield of 4f.
    • (1999) Synthesis , pp. 306-311
    • Numata, A.1    Kondo, Y.2    Sakamoto, T.3
  • 20
    • 0001038677 scopus 로고
    • Grethe, G., Ed.; John Wiley & Sons: New York
    • For a discussion of the Bischler-Napieralski reaction and other related synthetic strategies, see: Kametani, T.; Fukumoto, K. In Isoquinolines. Grethe, G., Ed.; John Wiley & Sons: New York, 1981; Part I, pp 139-274.
    • (1981) Isoquinolines , Issue.1 PART , pp. 139-274
    • Kametani, T.1    Fukumoto, K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.