Abstract
2-Cyclopropylthiazole hydrobromides undergo iminocyclopropane-pyrroline rearrangement in a melt to give the corresponding fused heterocycles, viz. 6,7-dihydro-5H-pyrrolo[2,1-b]thiazol-4-ium bromides. 2-Alkyl- and 2-aryl-4-cyclopropylthiazoles transform into analogous fused heterocycles as hydroiodides and noticeably longer.
References
1.
Tomilov Y.V., Platonov D.N., Frumkin A.E., Lipilin D.L., Salikov R.F.
Tetrahedron Letters,
2010
2.
Cloke J.B.
Journal of the American Chemical Society,
1929
3.
Stevens R.V., Ellis M.C., Wentland M.P.
Journal of the American Chemical Society,
1968
4.
Soldevilla A., Sampedro D.
Organic Preparations and Procedures International,
2007
5.
Kuduk S.D., Ng C., Chang R.K., Bock M.G.
Tetrahedron Letters,
2003
6.
Bailey T., Bremner J., Pelosi L., Skelton B., White A.
Australian Journal of Chemistry,
1995
7.
A. V. Samet, S.I. Firgang and V. V. Semenov, Khim. Geterotsikl. Soedin., 2005, 914 [Chem. Heterocycl. Compd. (Engl. Transl.), 2005, 41, 792].
8.
10.1016/j.mencom.2013.01.007_bib0040
Dyachenko
Zh. Org. Khim.,
2012
9.
Caldarelli S.A., Boisbrun M., Alarcon K., Hamzé A., Ouattara M., Salom-Roig X., Maynadier M., Wein S., Peyrottes S., Pellet A., Calas M., Vial H.
Bioorganic and Medicinal Chemistry Letters,
2010
10.
Hamzé A., Rubi E., Arnal P., Boisbrun M., Carcel C., Salom-Roig X., Maynadier M., Wein S., Vial H., Calas M.
Journal of Medicinal Chemistry,
2005
11.
12.
G. F. Field, J.R. Vermeulen and W. J. Zally, US Patent 5,001,140, A1, 1991.(Chem. Abstr., 1991, 113, 172006).
13.
D. Swinnen, C. Jorand-Lebrun, T. Grippi-Vallotton, P. Gerber, J. Gonzalez, J. Shaw and S. Jeyaprakashnarayanan, WO Patent 2010/100144, 2010.(Chem. Abstr., 2010, 153, 406429).
14.
Augustine J.K., Akabote V., Hegde S.G., Alagarsamy P.
Journal of Organic Chemistry,
2009
15.
I. Kinoyama, T. Miyazaki, Y. Koganemaru, N. Shiraishi, Y. Kawamoto and T. Washio, WO Patent 2010/090304, A1, 2010.
16.
10.1016/j.mencom.2013.01.007_bib0080
de Smet
Natuurwetenschappelijk Tijdschrift (Ghent),
1940
17.
L. L. Lincoln and D. W. Heseltine, Fr. Patent 1392489, 1965.(Chem. Abstr., 1966, 64, 3748c).