Abstract
The aza-Michael addition of primary nitraminofurazans to α,β-unsaturated carbonyl acceptors proceeds without a catalyst; the adducts or their 2,4-dinitrophenylhydrazones undergo retro-Michael fragmentation under basic conditions.
References
1.
V A. Smit and A. D. Dilman, Osnovy sovremennogo organicheskogo sinteza (Fundamentals of Modern Organic Synthesis), Binom, Moscow, [2009,] p. 233.(in Russian).
2.
Krishna P.R., Sreeshailam A., Srinivas R.
Tetrahedron,
2009
3.
Fridman A.L., Ivshin V.P., Novikov S.S.
Russian Chemical Reviews,
1969
4.
S. S. Novikov, G. A. Shveikhgeimer, V. V. Sevost’yanova and V. A. Shlyapochnikov, Khimiya alifaticheskikh i alitsiklicheskikh nitrosoedinenii (Chemistry of Aliphatic and Alicyclic Nitro Compounds), Khimiya, Moscow, 1974, p. 266.(in Russian).
5.
KISSINGER L.W., SCHWARTZ M.
Journal of Organic Chemistry,
1958
6.
FEUER H., MILLER R.
Journal of Organic Chemistry,
1961
7.
Kissinger L.W., Schwartz M., McQuistion W.E.
Journal of Organic Chemistry,
1961
8.
I. S. Ivanova, Yu. V. Konnova and S. S. Novikov, Izv. Akad. Nauk SSSR, Ser. Khim.,;1; 1962, 920.(Bull. Acad. Sci. USSR, Div. Chem. Sci., 1962, [11,] 858).
9.
10.1016/j.mencom.2010.11.016_bib0040
Ivanova
Izv. Akad. Nauk SSSR, Ser. Khim.,
1962
10.
10.1016/j.mencom.2010.11.016_bib0045
Ivanova
Izv. Akad. Nauk SSSR, Ser. Khim.,
1962
11.
Unterhalt B., Thamer D.
Archiv der Pharmazie,
1974
12.
10.1016/j.mencom.2010.11.016_bib0055
Vereshchagin
Zh. Org. Khim.,
1984
13.
10.1016/j.mencom.2010.11.016_bib0060
Marchenko
Zh. Org. Khim.,
1985
14.
10.1016/j.mencom.2010.11.016_bib0065
Spiridonova
Izv. Akad. Nauk, Ser. Khim.,
1999
15.
10.1016/j.mencom.2010.11.016_bib0070
Shitov
Izv. Akad. Nauk, Ser. Khim.,
2009
16.
10.1016/j.mencom.2010.11.016_bib0075
Luk’yanov
Izv. Akad. Nauk, Ser. Khim.,
1994
17.
10.1016/j.mencom.2010.11.016_bib0080
Luk’yanov
Izv. Akad. Nauk, Ser. Khim.,
1994
18.
A. B. Sheremetev, Ross. Khim. Zh. (Zh. Ross. Khim. Ob-va im. D. I. Mendeleeva), 1997, 41 (2), 43 [Mendeleev. Chem. J., 1997, 41 (2),.[62];].
19.
Sheremetev A.B., Kulagina V.O., Kryazhevskikh I.A., Melnikova T.M., Aleksandrova N.S.
Russian Chemical Bulletin,
2002
20.
A. B. Sheremetev and N. S. Aleksandrova, Izv. Akad. Nauk, Ser. Khim., 2005, 1665.(Russ. Chem. Bull., Int. Ed., 2005, 53, 1715).
21.
Suponitsky K.Y., Lyssenko K.A., Antipin M.Y., Aleksandrova N.S., Sheremetev A.B., Novikova T.S.
Russian Chemical Bulletin,
2009
22.
Sheremetev A.B., Aleksandrova N.S., Suponitsky K.Y., Antipin M.Y., Tartakovsky V.A.
Mendeleev Communications,
2010
23.
R. L.Willer, R. S. Day and D. J. Park, US Patent 5460669, 1995. (Chem. Abstr., 1996, 124, 33168).
24.
Dmitriev D.E., Strelenko Y.À., Sheremetev A.B.
Russian Chemical Bulletin,
2002
25.
Sheremetev A.B., Strelenko Y.A., Novikova T.S., Khmel'nitskii L.I.
Tetrahedron,
1993
26.
R. L. Forman, H. M. Mackinnon and P. D. Ritchie, J. Chem. Soc., C, [1968,] 2016.
27.
10.1016/j.mencom.2010.11.016_bib0105_2
Elguero
J. Chem. Res. (M),
1990
28.
Keiko N.A., Stepanova L.G., Kalikhman I.D., Voronkov M.G.
Russian Chemical Bulletin,
1983
29.
Ángeles García M., Claramunt R.M., Elguero J.
Magnetic Resonance in Chemistry,
2008
30.
L. I. Vereschagin, L. P. Kirillova, G. M. Luzgina and G. A. Gareev, Zh. Org. Khim., 1985, 21, 886 [J. Org. Chem. USSR (Engl. Transl.), 1985,.[21,] 806].