Abstract
Condensation of o-aminothiophenol with 2-hydroxy-3,4,5-tricarbalkoxycyclopentadienones gave 3a, 9-dihydro-3a-hydroxy-1,2,3-tricarbalkoxycyclopenta[b]-1,4-benzothiazines, which undergo dehydration to give 1,2,3-tricarbalkoxycyclopenta[b]-1,4-benzothiazines. The latter were characterized as π-electron analogs of azulene on the basis of their electronic and PMR spectra and quantum-chemical calculations.
Similar content being viewed by others
Literature cited
W. K. Hoga, US Patent No. 3148188 (1961); Chem. Abstr., 61, 13,326 (1964).
Umio Suminori and Noguchi Hiokyo, Japanse Patent No. 6927.588 (1969); Chem. Abstr., 72, 66,965 (1970).
D. Leaver, J. Smoliez, and W. T. Stafford, J. Chem. Soc., 740 (1962).
A. G. Anderson and W. F. Harrison, J. Amer. Chem. Soc., 86, 708 (1964).
G. F. Dvorko and T. F. Karpenko, USSR Author's Certificate No. 369117; Byull. Izobr., No. 10, 62 (1973).
N. V. Sumlivenko and G. F. Dvorko, Khim. Geterotsikl. Soedin., 134 (1974),
N. V. Sumlivenko, É. A. Ponomareva, G. G. Dyadyusha, and G. F. Dvorko, Khim. Geterotsikl. Soedin, 699 (1975).
B. I. Ionin and B. A. Ershov, Nuclear Magnetic Spectroscopy in Organic Chemistry [in Russian], Leningrad (1967), p. 302.
L. G. Kovalenko, L. K. Mushkalo, and V. A. Chiguk, in: Chemical Structures, Properties, and Reactivities of Organic Compounds [in Russian], Kiev (1969), p. 91.
W. Ried and W. Naek, ann., 745, 204 (1971).
A. Streitwieser, Molecular Orbital Theory for Organic Chemists, Wiley (1961).
Author information
Authors and Affiliations
Additional information
See [7] for communication I.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1078–1083, August, 1975.
Rights and permissions
About this article
Cite this article
Sumlivenko, N.V., Ponomareva, É.A., Dyadyusha, G.G. et al. New π-electron analogs of azulene. Chem Heterocycl Compd 11, 941–945 (1975). https://doi.org/10.1007/BF00470495
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00470495