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Volumn 69, Issue 15, 2004, Pages 4913-4924

Synthesis of pyrroles from 1-dialkylamino-3-phosphoryl(or phosphanyl)allenes through 1,5-cyclization of conjugated azomethine ylide intermediates

Author keywords

[No Author keywords available]

Indexed keywords

KETONES; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL); THERMODYNAMICS;

EID: 3543035212     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049586o     Document Type: Article
Times cited : (63)

References (51)
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    • Maas, G., Ed.; Thieme: Stuttgart
    • Black, D. StC. In Science of Synthesis; Maas, G., Ed.; Thieme: Stuttgart, 2001; Vol. 9, pp 441-552. Gossauer, A. In Houben-Weyl, Methoden der organischen Chemie; Kreher, R., Ed.; Thieme: Stuttgart 1994; Vol. E6a/1, pp 556-798. Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York 1994; Vol. 2, p 119. Jones, R. A. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley & Sons: New York 1990; Vol. 48, Part 1.
    • (2001) Science of Synthesis , vol.9 , pp. 441-552
    • Black, D.St.C.1
  • 2
    • 0042272181 scopus 로고
    • Kreher, R., Ed.; Thieme: Stuttgart
    • Black, D. StC. In Science of Synthesis; Maas, G., Ed.; Thieme: Stuttgart, 2001; Vol. 9, pp 441-552. Gossauer, A. In Houben-Weyl, Methoden der organischen Chemie; Kreher, R., Ed.; Thieme: Stuttgart 1994; Vol. E6a/1, pp 556-798. Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York 1994; Vol. 2, p 119. Jones, R. A. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley & Sons: New York 1990; Vol. 48, Part 1.
    • (1994) Houben-Weyl, Methoden der Organischen Chemie , vol.E6A-1 , pp. 556-798
    • Gossauer, A.1
  • 3
    • 0001426611 scopus 로고
    • Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York
    • Black, D. StC. In Science of Synthesis; Maas, G., Ed.; Thieme: Stuttgart, 2001; Vol. 9, pp 441-552. Gossauer, A. In Houben-Weyl, Methoden der organischen Chemie; Kreher, R., Ed.; Thieme: Stuttgart 1994; Vol. E6a/1, pp 556-798. Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York 1994; Vol. 2, p 119. Jones, R. A. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley & Sons: New York 1990; Vol. 48, Part 1.
    • (1994) Comprehensive Heterocyclic Chemistry II , vol.2 , pp. 119
    • Sundberg, R.J.1
  • 4
    • 3543033346 scopus 로고
    • Taylor, E. C., Ed.; Wiley & Sons: New York
    • Black, D. StC. In Science of Synthesis; Maas, G., Ed.; Thieme: Stuttgart, 2001; Vol. 9, pp 441-552. Gossauer, A. In Houben-Weyl, Methoden der organischen Chemie; Kreher, R., Ed.; Thieme: Stuttgart 1994; Vol. E6a/1, pp 556-798. Sundberg, R. J. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York 1994; Vol. 2, p 119. Jones, R. A. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley & Sons: New York 1990; Vol. 48, Part 1.
    • (1990) The Chemistry of Heterocyclic Compounds , vol.48 , Issue.PART 1
    • Jones, R.A.1
  • 13
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    • 3543020212 scopus 로고    scopus 로고
    • ref 12b
    • (d) ref 12b.
  • 30
    • 3542995616 scopus 로고    scopus 로고
    • note
    • A diagnostic test for the presence of this and all other pyrroles reported in this study was provided by the strong fluorescence on a TLC plate upon irradiation with 366 nm light.
  • 34
    • 3543033940 scopus 로고    scopus 로고
    • note
    • In particular, the H,H coupling constants indicate that the angular hydrogen 12b-H occupies an equatorial position at the chairlike morpholine or piperazine ring. In the NOESY spectrum, 12b-H shows a weak correlation peak with 7-H but not with 6-H.
  • 39
    • 3542993171 scopus 로고    scopus 로고
    • note
    • 3CN, 140 °C, 12 h) and in lower yield than aminoallene 4a itself. This suggests that the thermal conversion of aminoallenes 4 reported in this study does not proceed via their C-protonated form.
  • 40
    • 3543007065 scopus 로고    scopus 로고
    • Doctoral Thesis, University of Ulm
    • J. Schlegel, Doctoral Thesis, University of Ulm, 1999.
    • (1999)
    • Schlegel, J.1
  • 46
    • 0009475471 scopus 로고
    • Höft, E.; Katritzky, A. R.; Nesbit, M. R. Tetrahedron Lett. 1967, 3041-3044; 1968, 2028.
    • (1968) Tetrahedron Lett. , pp. 2028


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.