Abstract
Tartaric acid–zinc nitrate has been found to be an efficient Brønsted acid-assisted Lewis acid catalytic system for the facile synthesis of β-amino carbonyl compounds through the one-pot Mannich reaction of aldehydes, aromatic amines and ketones in ethanol at room temperature. Remarkable enhancement of reactivity by tartaric acid (Brønsted acid) was observed in these reactions in the presence of anhydrous zinc nitrate (Lewis acid), due to coordination of the tartaric acid ligand to zinc ions increasing the acidity of the system. This procedure shows some advantages such as mild reaction conditions, short reaction times and high yields.
References
1.
Filho J.F.A.
,
Lemos B.C.
,
de Souza A.S.
,
Pinheiro S.
, and
Greco S.J.
, Tetrahedron , 2017 , 73 , 6977 .
2.
Salim S.
,
Ann H.N.
,
Keerthi K.K.
, and
Gopinathan A.
, Asian J. Org. Chem. , 2018 , 7 , 613 .
3.
Zhao G.
,
Jiang T.
,
Gao H.
,
Han B.
,
Huang J.
, and
Sun D.
, Green Chem. , 2004 , 6 , 75 .
4.
Alvim H.G.O.
,
Bataglion G.A.
,
Ramos L.M.
,
de Oliveira A.L.
,
de Oliveira H.C.B.
,
Eberlin M.N.
,
de Macedo J.L.
,
da Silva W.A.
, and
Neto B.A.D.
, Tetrahedron , 2014 , 70 , 3306 .
5.
Kidwai M.
,
Mishra N.K.
,
Bansal V.
,
Kumar A.
, and
Mozumdar S.
, Tetrahedron Lett. , 2009 , 50 , 1355 .
6.
Zetchi A.
,
Boumoud B.
,
Boumoud T.
, and
Debache A.
, Der Pharma Chem. , 2016 , 8 , 84 .
7.
Manabe K.
,
Mori Y.
, and
Kobayashi S.
, Tetrahedron , 2001 , 57 , 2537 .
8.
Chaitanya M.
, and
Anbarasan P.
, Org. Lett. , 2018 , 20 , 3362 .
9.
Mouhtady O.
,
Gaspard-Iloughmane H.
,
Roques N.
, and
Le Roux C.
, Tetrahedron Lett. , 2003 , 44 , 6379 .
10.
Manabe K.
,
Mori Y.
,
Nagayama S.
,
Odashima K.
, and
Kobayashi S.
, Inorg. Chim. Acta , 1999 , 296 , 158 .
11.
Hatano M.
,
Goto Y.
,
Izumiseki A.
,
Akakura M.
, and
Ishihara K.
, J. Am. Chem. Soc. , 2015 , 137 , 13472 .
12.
Aspinall H.C.
,
Bissett J.S.
,
Greeves N.
, and
Levin D.
, Tetrahedron Lett. , 2002 , 43 , 319 .
13.
Liu Q.
,
Ai H.M.
, and
Feng S.
, Synth. Commun. , 2012 , 42 , 122 .
14.
Wang M.
,
Gao J.
, and
Song Z.
, Z. Naturforsch. B , 2010 , 65 , 1349 .
15.
Vangala V.B.
, and
Pati H.N.
, Synth. Commun. , 2016 , 46 , 374 .
16.
Coronado E.
,
Galán-Mascarós J.R.
,
Gómez-García C.J.
, and
Murcia-Martínez A.
, Chem. A Euro. J. , 2006 , 12 , 3484 .
17.
Hyung L.W.
,
Hak B.I.
,
Moon K.B.
, and
Young-Bae S.
, Bull. Korean Chem. Soc. , 2016 , 37 , 1910 .
18.
Li H.
,
Zeng H.
, and
Shao H.
, Tetrahedron Lett. , 2009 , 50 , 6858 .
19.
Eshghi H.
, and
Yazdi H.P.
, J. Sci. , 2003 , 14 , 17 .
20.
Liu Q.
,
Qiao Y.
,
Tian Y.
,
Gu F.
,
Zhong Z.
, and
Su F.
, Ind. Eng. Chem. Res. , 2017 , 56 , 9809 .
21.
Liu Q.
,
Wang S.
,
Zhao G.
,
Yang H.
,
Yuan M.
,
An X.
,
Zhou H.
,
Qiao Y.
, and
Tian Y.
, Int. J. Hydrogen Energy , 2018 , 43 , 239 .
22.
Dömling A.
, Chem. Rev. , 2006 , 106 , 17 .
23.
Schwendt P.
,
Švančárek P.
,
Kuchta L.
, and
Marek J.
, Polyhedron , 1998 , 17 , 2161 .
24.
Lin H.
,
Hu H.
,
Chen B.
, and
Li J.
, Chin. J. Spectrosc. , 2009 , 26 , 803 .
25.
Bélanger G.
,
Doré M.
,
Ménard F.
, and
Darsigny V.
, J. Org. Chem. , 2006 , 71 , 7481 .
26.
Lu G.
, and
Cai C.
, Catal. Commun. , 2010 , 11 , 745 .
27.
Yi W.B.
, and
Cai C.
, J. Fluorine Chem. , 2006 , 127 , 1515 .
28.
Gong K.
,
Fang D.
,
Wang H.L.
, and
Liu Z.L.
, Monatsh. Chem. , 2007 , 138 , 1195 .
29.
Dong F.
,
Zhenghao F.
, and
Zuliang L.
, Catal. Commun. , 2009 , 10 , 1267 .
30.
Barbero M.
,
Cadamuro S.
, and
Dughera S.
, Tetrahedron: Asymmetry , 2015 , 26 , 1180 .
31.
Wang R.
,
Li B.
,
Huang T.
,
Shi L.
, and
Lu X.
, Tetrahedron Lett. , 2007 , 48 , 2071 .
32.
Zhang Y.
,
Han J.
, and
Liu Z.
, RSC Adv. , 2015 , 5 , 25485 .
33.
Chen X.
,
Sun H.
,
Luo Y.
,
Jian Y.
,
Wu Y.
,
Zhang W.
, and
Gao Z.
, RSC Adv. , 2016 , 6 , 39343 .
34.
Ollevier T.
,
Nadeau E.
, and
Guay-Bégin A.A.
, Tetrahedron Lett. , 2006 , 47 , 8351 .
35.
Azizi N.
, and
Edrisi M.
, Microporous Mesoporous Mater. , 2017 , 240 , 130 .