Abstract
β-Amino secondary alcohols were formed by aminolysis of epichlorohydrin and styrene oxide with aromatic amines using aqueous ethanol (1:1) as the solvent in conjunction with microwave irradiation without a catalyst. The methodology is fast, efficient, highly regioselective, chemoselective and environmentally benign.
References
1.
Joossens J.
,
Van der Veken P.
,
Lambeir A.M.
,
Augustyns K.
, and
Haemers A.
, J. Med. Chem. , 2004 , 47 , 2411 .
2.
Corey E.J.
, and
Zhang F.
, Angew. Chem., Int. Ed. , 1999 , 38 , 1931 .
3.
Fagnou K.
, and
Lautens M.
, Org. Lett. , 2000 , 2 , 2319 .
4.
Rodríguez J.R.
, and
Navarro A.
, Tetrahedron Lett. , 2004 , 45 , 7495 .
5.
Sundararajan G.
,
Vijayakrishna K.
, and
Varghese B.
, Tetrehedron Lett. , 2004 , 45 , 8253 .
6.
Carree F.
,
Gil R.
, and
Collin J.
, Org. Lett. , 2005 , 7 , 1023 .
7.
Azoulay S.
,
Manabe K.
, and
Kobayashi S.
, Org. Lett. , 2005 , 7 , 4593 .
8.
Kokubo M.
,
Naito T.
, and
Kobayashi S.
, Tetrahedron , 2010 , 66 , 1111 .
9.
Chakravarti R.
,
Oveisi H.
,
Kalita P.
,
Pal R.R.
,
Halligudi S.B.
,
Kantam M.L.
, and
Vinu A.
, Microporous Mesoporous Mater. , 2009 , 123 , 338 .
10.
Robinson M.W.C.
,
Davies A.M.
,
Mabbett I.
,
Davies T.E.
,
Apperley D.C.
,
Taylor S.H.
, and
Graham A.E.
, J. Mol. Catal. A: Chem. , 2010 , 329 , 57 .
11.
Karimian R.
,
Piri B.
, and
Abolghasem M.
, Chin. J. Chem. , 2011 , 29 , 955 .
12.
Wu J.
, and
Xia H.-G.
, Green Chem. , 2005 , 7 , 708 .
13.
Shivani
,
Pujala B.
, and
Chakraborti A.K.
, J. Org. Chem. , 2007 , 72 , 3713 .
14.
Chimni S.S.
,
Bala N.
,
Dixit V.A.
, and
Bharatam P.V.
, Tetrahedron , 2010 , 66 , 3042 .
15.
Azizi N.
, and
Saidi M.R.
, Org. Lett. , 2005 , 7 , 3649 .
16.
Wang Z.
,
Cui Y.T.
,
Xu Z.B.
, and
Qu J.
, J. Org. Chem. , 2008 , 73 , 2270 .
17.
Robin A.
,
Brown F.
,
Rosa N.B.
,
Wu B.
,
Beitz E.
,
Kun J.F.J.
, and
Flitsch S.L.
, J. Med. Chem. , 2007 , 50 , 4243 .
18.
Du Z.
,
Wang F.
,
Zhou W.
, and
Wang J.-X.
, J. Chem. Res. , 2010 , 34 , 475 .
19.
Du Z.
,
Zhou W.
,
Wang F.
, and
Wang J.-X.
, Tetrahedron , 2011 , 67 , 4914 .
20.
Du Z.
,
Zhou W.
,
Bai L.
,
Wang F.
, and
Wang J.-X.
, Synlett , 2011 , 369 .
21.
Gupta P.
,
Bhatia S.
,
Dhawan A.
,
Balwani S.
,
Sharma S.
,
Brahma R.
,
Singh R.
,
Ghosh B.
,
Parmar V.S.
, and
Prasad A.K.
, Bioorg. Med. Chem. , 2011 , 19 , 2263 .
22.
Kamal A.
,
Prasad B.R.
,
Reddy A.M.
, and
Khan M.N.
, Catal. Commun. , 2007 , 8 , 1876 .
23.
Danafar H.
, and
Yadollahi B.
, Catal. Commun. , 2009 , 10 , 842 .
24.
Saikia L.
,
Satyarthi J.K.
,
Srinivas D.
, and
Ratnasamy K.
, J. Catal. , 2007 , 252 , 148 .
