Abstract
Ethyl 3-aminobut-2-enoates MeC(NHR)=CHCO2Et (R = H, Me, Bn) whose reaction site is C(2) atom add to 2-R-3-nitro-2H-chromenes at their C(4) atom to give the corresponding trans,trans-2,3,4-trisubstituted chromanes. Analogous substrates MeC(NR2)=CHCO2Et (NR2 is piperidin-1-yl or morpholin-4-yl) react by their C(4) methyl group to afford cis,trans-2,3,4-trisubstituted chromanes. The stereochemistry of the products was established by X-ray diffraction analysis.
References
2.
Bowers W.S., Ohta T., Cleere T., Marsella P.A.
Science,
1976
3.
Bergmann R., Gericke R.
Journal of Medicinal Chemistry,
1990
4.
G. Burrell, F. Cassidy, J.M. Evans, D. Lightowler and G. Stemp, J. Med. Chem., 1990, 33, 3023.
5.
Gericke, J. Harting, I. Lues and C. Schittenhelm,;1; J. Med. Chem., 1991, 34, 3074.
6.
7.
Yoshikoshi A., Miyashita M.
Accounts of Chemical Research,
1985
8.
Korotaev V., Sosnovskikh V., Kutyashev I., Kodess M.
Letters in Organic Chemistry,
2005
9.
V. Yu. Korotaev, V. Ya. Sosnovskikh, B. Kutyashev and M. I. Kodess, Russ. Chem. Bull., Int. Ed., 2006, 55, 317 (Izv. Akad. Nauk, Ser. Khim., 2006, 309).
10.
V. Yu. Korotaev, V. Ya. Sosnovskikh, I.B. Kutyashev and M. I. Kodess, Russ. Chem. Bull., Int. Ed., 2006, 55, 2020 (Izv. Akad. Nauk, Ser. Khim., 2006, 1945).
11.
Korotaev V.Y., Kutyashev I.B., Sosnovskikh V.Y., Kodess M.I.
Mendeleev Communications,
2007
12.
V. Yu. Korotaev, V. Ya. Sosnovskikh and I. B. Kutyashev, Russ. Chem. Bull., Int. Ed., 2007, 56, 2054 (Izv. Akad. Nauk, Ser. Khim., 2007, 1985).
13.
V. Yu. Korotaev, V. Ya. Sosnovskikh, M.A. Barabanov, E.S. Yasnova, M.A. Ezhikova, M.I. Kodess and P. A. Slepukhin, Tetrahedron, 2010, 66, 1404.
14.
V. Yu. Korotaev, V. Ya. Sosnovskikh, A. Yu. Barkov, P.A. Slepukhin, M.A. Ezhikova, M.I. Kodess and Yu. V. Shklyaev, Tetrahedron, 2011, 67, 8685.
15.
S. Biswas, P.R. Maulik, R.C. Gupta, M. Seth and A. P. Bhaduri, Acta Crystallogr., Sect. C, 1996, 52, 1036.
16.
Lin C., Hsu J., Sastry M.N., Fang H., Tu Z., Liu J., Ching-Fa Y.
Tetrahedron,
2005
17.
R. C. Gupta, M. Seth and A. P. Bhaduri, Indian J. Chem., 1991, 30B, 297.
18.
V. Yu. Korotaev, A. Yu. Barkov, P.A. Slepukhin, M.I. Kodess and V. Ya. Sosnovskikh, Tetrahedron Lett., 2011, 52, 5764.
19.
Sheldrick G.M.
Acta Crystallographica Section A Foundations of Crystallography,
2007