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Volumn 43, Issue 4, 2006, Pages 963-977

Azulene-substituted pyranylium salts. Syntheses and products characterization

Author keywords

[No Author keywords available]

Indexed keywords

2,6 DIMETHYLPYRANILIUM SALT; 2,6 DIPHENYLPYRANILIUM SALT; 4 AZULENE; 4,6 DIMETHYLPYRANILIUM SALT; AZULENE; PYRANILIUM SALT; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

EID: 33747409050     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570430423     Document Type: Article
Times cited : (19)

References (36)
  • 1
    • 33847521641 scopus 로고    scopus 로고
    • European Patent 837141 (1998)
    • T. Okamoto and N. Yamamoto, European Patent 837141 (1998); Chem. Abstr., 128, 291125g (1998).
    • (1998) Chem. Abstr. , vol.128
    • Okamoto, T.1    Yamamoto, N.2
  • 2
    • 85056674579 scopus 로고
    • European Patent 659407 (1995)
    • T. Okamoto, N. Yamamoto, European Patent 659407 (1995); Chem. Abstr., 123, 221957c (1995).
    • (1995) Chem. Abstr. , vol.123
    • Okamoto, T.1    Yamamoto, N.2
  • 3
    • 25044481015 scopus 로고
    • US Patent. 4,971,891 (1990)
    • K. Kawamura, Y. Okamoto, US Patent. 4,971,891 (1990); Chem. Abstr., 111, 222173h (1989).
    • (1989) Chem. Abstr. , vol.111
    • Kawamura, K.1    Okamoto, Y.2
  • 12
    • 0035824058 scopus 로고    scopus 로고
    • Our previous attempt to obtain 2,4,6-tri(azulen-1-yl)-pyranylium salts starting from corresponding carbonylic compounds failed despite the chalcone generation. In this respect the research is in progress. A similar problem was encountered at the attempts to synthesize 2,4,6-tri(4-dimethylaminobenzene)- pyranylium salt that results only in traces: F. Sancenon, R. Martinez-Manez and J. Soto, Chem. Commun., 2262 (2001).
    • (2001) Chem. Commun. , pp. 2262
    • Sancenon, F.1    Martinez-Manez, R.2    Soto, J.3
  • 16
    • 33747397369 scopus 로고    scopus 로고
    • note
    • It must be observed the lack in information contained in references [7], [8] and [9] about the products purification; also it is not clear if the reported yields are calculated for raw or purified product.
  • 24
    • 33747429147 scopus 로고    scopus 로고
    • note
    • The MOPAC 7.0 package and AMI approache were used; key words: PULAY GNORM = 0.01 SHIFT = 50 GEO-OK CAMP-KING CHARGE = 1. Because the computed response for the three used programs, AMI, MNDO and PM3 was similar (e. g. for the dihedral angle in 4-(azulen-1-yl)-2,6-diphenylpyranylium the obtained values were 22.56°, 25.00° and 25.00°, respectively), the more used AM1 approach was selected for this work. The barriers to rotation (racemization) were calculated using PCMODEL.
  • 25
    • 33747420729 scopus 로고    scopus 로고
    • note
    • The study of UV/Vis spectra on a performing device is in progress and the results will be discussed in another paper.
  • 27
    • 84979190806 scopus 로고
    • The deuterium exchange seems to be promoted by traces of perchloric acid remaining from the work-up; the addition of a very small amount of triethylamine avoids the exchange. Similar exchanges were reported by E. Garg, A. Vasilescu, G. D. Mateescu and A. T. Balaban, J. Labelled Compd., 3, 196, (1967).
    • (1967) J. Labelled Compd. , vol.3 , pp. 196
    • Garg, E.1    Vasilescu, A.2    Mateescu, G.D.3    Balaban, A.T.4
  • 30
    • 33747384332 scopus 로고    scopus 로고
    • note
    • The alkyl groups at seven-membered ring in azulene also contribute to the increase in electron density.
  • 31
    • 33747404268 scopus 로고    scopus 로고
    • note
    • Pyranylium salts are stable at 20 eV when the signal of molecular ion is present. At 40 eV, however, the molecular ion is broken in several fragments which allow subsequent complicated reaction.
  • 34
    • 33747413757 scopus 로고    scopus 로고
    • note
    • The higher solubility of the tetrafuoroborate compared to perchlorate enable us the better characterization of the salt.
  • 35
    • 33747399098 scopus 로고    scopus 로고
    • note
    • It must be signaled that, even at 500 MHz, the signals of azulenic protons at 2′ and 3′ are a bright singlet and not a doublet as expected.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.