The reaction of 2,3-dibromo-1,4-naphthoquinone with 2-aminothiazole in MeONa/MeOH at 60oC for 3 h gave naphtho[2',3':4,5]imidazo[2,1-b][1,3]thiazole-5,10-dione in 64% yield. The reaction of 2,3-dibromo-1,4-naphthoquinone with 2-aminobenzothiazole under the above-mentioned conditions gave 2-(benzo[d]thiazol-2-ylamino)-3-bromonaphthalene-1,4-dione in 64% yield, which on treatment with Na/THF or NaN3/acetone under reflux conditions gave naphtho[2',3':4,5]imidazo[2,1-b][1,3]- benzothiazole-7,12-dione in 69 and 56% yields, respectively.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
G. Zinke, Ber., 20, 1514 (1887).
S. M. McElrain and E. L. Engelhard, J. Am. Chem. Soc., 66, 1077 (1994).
S. William and J. Partick, Tetrahedron Lett., 33, 53 (1992).
Y. Ueno, K. Maeda, J. Koshitani, and T. Yoshida, J. Heterocycl. Chem., 19, 189 (1982).
M. M. Baradarani, J. Khalafy, S. Khadivi, and A. Poursattar Marjani, Khim. Geterotsikl. Soedin., 751 (2008). [Chem. Heterocycl. Comp., 44, 594 (2008) ].
J. Khalafy, A. Poursattar Marjani, and A. R. Molla Ebrahimlo, J. Braz. Chem. Soc., 17, 570 (2006).
D. D. Perrin and W. L. F. Armarego, Purification of Laboratory Chemicals, Pergamon Press: Oxford (UK), 1988, p. 20.
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 769-772. May, 2010.
Rights and permissions
About this article
Cite this article
Khalafy, J., Ghezelbash, Z.D. & Mahmoody, M. Synthesis of naphtho[2',3':4,5]imidazo[2,1-b][1,3]-thiazole-5,10-dione and naphtho[2',3':4,5]imidazo-[2,1-b][1,3]benzothiazole-7,12-dione. Chem Heterocycl Comp 46, 613–616 (2010). https://doi.org/10.1007/s10593-010-0554-6
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-010-0554-6