Abstract
Terminal alkynols react with formaldehyde and secondary amines in aqueous ionic liquid [emim]HSO–4 in the presence of Cu(OAc) to afford the corresponding 1-(a-hydroxyalkyl)- or 1-(b-hydroxyalkyl)-2-(aminomethyl)acetylenes in better yields in comparison with the reaction in conventional organic solvents. The catalytic system can be easily recovered and recycled.
References
1.
Konishi M., Ohkuma H., Tsuno T., Oki T., VanDuyne G.D., Clardy J.
Journal of the American Chemical Society,
1990
2.
V. M. Kurilenko, G.N. Khlienko, L.M. Moiseeva, D.V. Sokolov, K.D. Praliev and N. A. Belikova, Khim. Farm. Zh., 1976, 10, 60 (in Russian).
3.
Osadchii S.A., Shults E.E., Polukhina E.V., Shakirov M.M., Vasilevskii S.F., Stepanov A.A., Tolstikov G.A.
Russian Chemical Bulletin,
2007
4.
Dembitsky V.M., Levitsky D.O.
Natural Product Communications,
2006
5.
Schulte K.E., Rücker G.
1970
6.
C. L. Zirkle and C. Kaiser, in Psychopharmacological Agents, ed. M. Gordon, Academic Press, New York, 1964, vol. 1, pp. 445-554.
7.
V. F. Kucherov, M.V. Mavrov and A. R. Derginskii, Prirodnye poli- atsetilenovye soedineniya (Natural Polyacetylene Compounds), Nauka, Moscow, 1972 (in Russian).
8.
Tramontini M., Angiolini L.
Tetrahedron,
1990
9.
Cho A.K., Haslett W.L., Jenden D.J.
Biochemical and Biophysical Research Communications,
1961
10.
(a)M. Negwer, Organisch-chemische Arzneimittel und ihre Synonyma, Academie Verlag, Berlin, 1971, vol. 1;
11.
(b) J. L. Hirtz, Analytical Metabolic Chemistry of Drugs, Marcel Dekker, New York, 1971.
12.
Kabdraisova A.Z., Faskhutdinov M.F., Yu V.K., Praliev K.D., Fomicheva E.E., Shin S.N., Berlin K.D.
Chemistry of Natural Compounds,
2007
13.
Kantam M.L., Prakash B.V., Reddy C.R., Sreedhar B.
Synlett,
2005
14.
Mannich C., Chang F.T.
Berichte der deutschen chemischen Gesellschaft (A and B Series),
1933
15.
Jones E.R., Marszak I., Bader H.
Journal of the Chemical Society (Resumed),
1947
16.
(a) I. N. Nazarov and G. A. Shvekhgeimer, Zh. Obshch. Khim., 1956, 26, 813 (in Russian);
17.
(b) I. N. Nazarov, R.I. Kruglikova and G. I. Nikolaev, Zh. Obshch. Khim., 1959, 29, 1859 (in Russian).
18.
Shvekhgeimer G.A.
Russian Chemical Bulletin,
1958
19.
HENNION G.F., BOISSELLE A.P.
Journal of Organic Chemistry,
1961
20.
Simirskaya N.I., Mavrov M.V., Kucherov V.F.
Russian Chemical Bulletin,
1977
21.
Mavrov M.V., Zlotin S.G.
Russian Chemical Bulletin,
2007
22.
Mavrov M.V., Zlotin S.G.
Russian Chemical Bulletin,
2009
23.
P. Dimrath, P. Duffner, R. Oster and H. Paedach, German Patent 1.100.617, 1961 (Chem. Abstr., 1961, 55, 19960f).
24.
Wang M., Li P., Wang L.
European Journal of Organic Chemistry,
2008
25.
Gevorkyan A.A., Arakelyan A.S., Movsisyan A.A., Dzhandzulyan Z.L., Petrosyan K.A.
Russian Journal of General Chemistry,
2006
26.
An efficient synthesis of propargylamines via C–H activation catalyzed by copper(i ) in ionic liquids
Park S.B., Alper H.
Chemical Communications,
2005
27.
Yadav J.S., Subba Reddy B.V., Naveenkumar V., Srinivasa Rao R., Nagaiah K.
New Journal of Chemistry,
2004
28.
Li Z., Wei C., Chen L., Varma R.S., Li C.
Tetrahedron Letters,
2004
29.
Li C., Wei C.
Chemical Communications,
2002
30.
Chen W., Nguyen R.V., Li C.
Tetrahedron Letters,
2009
31.
Zhang Y., Li P., Wang M., Wang L.
Journal of Organic Chemistry,
2009
32.
Dallinger D., Kappe C.O.
Chemical Reviews,
2007
33.
Patil M.K., Keller M., Reddy B.M., Pale P., Sommer J.
European Journal of Organic Chemistry,
2008
34.
Ionic Liquids in Synthesis, 2nd edn., eds. P. Wasserscheid and T. Welton, Wiley-VCH, Weinheim, 2008.
35.
Zlotin S.G., Makhova N.N.
Mendeleev Communications,
2010
36.
Zlotin S.G., Makhova N.N.
Russian Chemical Reviews,
2010
37.
Kucherenko A.S., Syutkin D.E., Zlotin S.G.
Russian Chemical Bulletin,
2008
38.
Wei C., Li C.
Journal of the American Chemical Society,
2003
39.
Z. Li and C.-J. Li, Org. Lett., 2003, 5, 4475.
40.
Shi L., Tu Y., Wang M., Zhang F., Fan C.
Organic Letters,
2004
41.
M. Tramontini and L. Angiolini, Mannich-Bases, Chemistry and Uses, CRC Press, Boca Raton, 1994.