Abstract
A preparative route is proposed for the synthesis of the novel heterocyclic systems 7-oxo- and 1,2,7-trioxo-1,2-dihydropyrano[3,2-e]indole using classical Fischer and Sandmeyer methods respectively. We have studied various conditions for cyclization of the starting coumarin 6-isonitrosoacetamide and the methyl or ethyl pyruvate 6-coumarinylhydrazones. The syn- and anti-form ratio of the latter and the structure of all of the synthesized compounds were determined using spectroscopic data analysis.
Similar content being viewed by others
REFERENCES
T. E. Khoshtariya, M. L. Kakhabrishvili, M. I. Sikharulidze, L. N. Kurkovskaya, and N. N. Suvorov, Khim. Geterotsikl. Soedin., 355 (1985).
T. E. Khoshtariya, T. O. Dzhashi, and L. N. Kurkovskaya, Khim. Geterotsikl. Soedin., 627 (1999).
T. O. Dzhashi, T. E. Khoshtariya, L. N. Kurkovskaya, N. T. Mirziashvili, and M. I. Sikharulidze, Khim. Geterotsikl. Soedin., 1419 (1999).
T. E. Khoshtariya, L. T. Bochoidze, and K. T. Batsikadze, Khim. Geterotsikl. Soedin., 624 (2004).
M. D. Mashkovskii, Drugs [in Russian], Meditsina, Moscow (1984), Chapter 2, p. 190.
E. V. Naumenko and N. K. Popova, in Serotonin and Melatonin in the Regulation of the Endocrine System [in Russian], Nauka, Siberian Section, Novosibirsk (1975), p. 145.
M. D. Mashkovskii, Drugs [in Russian], Meditsina, Moscow (1984), Chapter 1, p. 112.
T. O. Soine, J. Pharm. Sci., 53, 231 (1964).
H. Bayerle and R. Marx, Biochem. Z., 319, 18 (1948).
Z. Prochaska, Ceskosl. Farm., 3, 221 (1954).
C. Schroeder, S. Preis, and K. P. Link, Tetrahedron Lett., 23 (1960).
J. K. Sugden and T. O. Yoloye, Pharm. Acta Helv., 53, No.3/4, 65 (1978).
Author information
Authors and Affiliations
Additional information
Dedicated to the memory of a dear teacher, the prominent Russian science professor Nikolai Nikolaevich Suvorov. Founder of indole chemistry in Georgia. In love with, and a warm favourite of, Georgia.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 238–245, February, 2005.
Rights and permissions
About this article
Cite this article
Khoshtariya, T.E., Kurkovskaya, L.N., Bochoidze, L.T. et al. Pyrrolocoumarins. 1. Synthesis and Spectroscopic Investigation of 7-Oxo- and 1,2,7-Trioxo-1,2-dihydropyrano-[3,2-e]indole and Their Derivatives. Chem Heterocycl Compd 41, 208–215 (2005). https://doi.org/10.1007/s10593-005-0129-0
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s10593-005-0129-0