Abstract
The reaction of isocyanates and isothiocyanates with 2-indolylurethanes takes place primarily in the 3 position of the indole ring to give the corresponding amides and thioamides, which smoothly undergo cyclization when they are heated with sodium ethoxide to give the corresponding quinazoline derivatives.
Similar content being viewed by others
Literature cited
E. P. Papandopoulos and S. B. Bedrosian, J. Org. Chem., 33, 4551 (1968).
M. Seefelder, Chem. Ber., 96, 3243 (1963).
J. M. Weinmann, Diss. Abstr., 25, 1588 (1958).
L. Elvidge and F. Spring, J. Chem. Soc., Suppl. Issue No. 1, 135 (1949).
A. Deberly and J. Bourdais, Tetrahedron Lett., No. 32, 3049 (1971).
R. Pschorr and G. Hoppe, Ber., 43, 2543 (1910).
C. W. Whitehead and J. Traverso, J. Am. Chem. Soc., 80, 962 (1958).
Yu. S. Nekrasov, P. A. Sharbatyan, R. S. Sagitullin, V. A. Puchkov, A. N. Kost, and N. S. Vul'fson, Izv. Akad. Nauk SSSR, Ser. Khim., No. 10, 2181 (1969).
C. P. Lewis, Anal. Chem., 36, 1582 (1964).
A. N. Kost, R. S. Sagitullin, T. Jagodzinski, and V. V. Men'shikov, Vestn. Mosk. Gos. Univ. Ser. Khim., 618 (1976).
K. Shudo and T. Okamoto, Tetrahedron, 33, 1717 (1977).
S. Niementowski, J. Prakt. Chem., 51, 564 (1895).
F. Russo and M. Gelardoni, Ann. Chim. (Roma), 56, 839 (1966); Chem. Abstr., 66, 18696 (1967).
W. Dymec and B. Lucka-Sobstel, Diss. Pharm., 17, 196 (1965); Chem. Abstr., 63, 16347 (1965).
A. J. Frey, G. E. Hardtman, and H. Ott, US Patent No. 3414574 (1967); Chem. Abstr., 70, 47490 (1969).
J. H. Bowie, S. O. Lawesson, J. Q. Madson, G. Schroll, and D. H. Williams, J. Chem. Soc., B, No. 10, 951 (1966).
A. N. Kost, T. Jagodzinski, and R. S. Sagitullin, Khim. Geterotsikl. Soedin., No. 5, 706 (1977).
Y. Sakuma and F. Yoneda, Heterocycles, 6, 1911 (1977).
V. I. Gorbunov, A. N. Kost, and R. S. Sagitullin, Khim.-Farm. Zh., No. 9, 12 (1968).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 214–223, February, 1979.
Rights and permissions
About this article
Cite this article
Jagodzinski, T., Kost, A.N. & Sagitullin, R.S. 3-carbamido-2-indolylurethanes and their cyclization to pyrimido[4,5-b] indoles. Chem Heterocycl Compd 15, 179–187 (1979). https://doi.org/10.1007/BF00480364
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00480364