Abstract
An efficient synthetic protocol for 2-(1-aryl-2-nitroethyl)-3-arylaminoacrylates
was successfully developed by the one-pot domino reaction of arylamines,
methyl propiolate, and nitrostyrenes. The reaction involves the
formation of β-enamino ester and its sequential Michael
addition to nitrostyrene.
Key words
domino reaction - β-enamino ester - electron-deficient alkyne - nitrostyrene - acrylate
References
1a
Lue P.
Greenhill JV.
Adv.
Heterocycl. Chem.
1997,
67:
215
1b
Elassara AZ.
El-Khair AA.
Tetrahedron
2003,
59:
8463
2a
Bagley MC.
Dale JW.
Bower J.
Chem. Commun.
2002,
1682
2b
Valla A.
Valla B.
Cartier D.
Le Guillou R.
Labia R.
Potier P.
Tetrahedron Lett.
2005,
46:
6671
3a
Katritzky AR.
Hayden AE.
Kirichenko K.
Pelphrey P.
Ji Y.
J. Org. Chem.
2004,
69:
5108
3b
Cunha S.
Damasceno F.
Ferrari J.
Tetrahedron
Lett.
2007,
48:
5795
3c
Kikuchi S.
Iwai M.
Murayama H.
Fukuzaka S.
Tetrahedron Lett.
2008,
49:
114
4a
Vohra RK.
Bruneau C.
Renaud J.
Adv. Synth. Catal.
2006,
348:
2571
4b
Kumar A.
Maurya RA.
Tetrahedron
2008,
64:
3477
4c
Moreau J.
Duboc A.
Hubert C.
Hurvois J.-P.
Renaud JL.
Tetrahedron
Lett.
2007,
48:
8647
4d
Sirijindalert H.
Hansuthirakul K.
Rashatasakhon P.
Sukwattanasinitt M.
Ajavakom A.
Tetrahedron
2010,
66:
5161
5a
Rechsteiner B.
Texier-Boullet F.
Hamelin J.
Tetrahedron Lett.
1993,
34:
5071
5b
Valduga CJ.
Squizani A.
Braibante HS.
Braibante MEF.
Synthesis
1998,
1019
5c
Arcadi A.
Bianchi G.
Di Giuseppe S.
Marinelli F.
Green Chem.
2003,
64
5d
Khosropour AR.
Khodaei MM.
Kookhazadeh M.
Tetrahedron Lett.
2004,
45:
1725
6a
Glotova T.
Dvorko M.
Ushakov I.
Chipanina N.
Kazheva O.
Chekhlov A.
Dyachenko O.
Gusarova N.
Trofimov B.
Tetrahedron
2009,
65:
9814
6b
Ziyaei-Halimehjani A.
Saidi MR.
Tetrahedron
Lett.
2008,
49:
1244
6c
Li X.
Wang JY.
Yu W.
Wu LM.
Tetrahedron
2009,
65:
1140
6d
Yavari I.
Bayat MJ.
Sirouspour M.
Souri S.
Tetrahedron
2010,
66 :
7995
7a
Nguyen TB.
Martel A.
Dhal R.
Dujardin G.
Org. Lett.
2008,
10:
4493
7b
Fan MQ.
Yan ZY.
Liu WM.
Liang YM.
J.
Org. Chem.
2005,
70:
8204
7c
Naidu BN.
Sorenson ME.
Org.
Lett.
2005,
7:
1391
7d
Madhav B.
Murthy SN.
Rao KR.
Venkata Y.
Nageswar D.
Helv.
Chim. Acta
2010,
93:
257
8a
Srikrishna A.
Sridharan M.
Prasad KR.
Tetrahedron Lett.
2010,
51:
3651
8b
Bezenšek J.
Koleša T.
Grošelj U.
Wagger J.
Stare K.
Meden A.
Svete J.
Stanovnik B.
Tetrahedron Lett.
2010,
51:
3392
8c
Alizadeh A.
Rostamnia S.
Hosseinpour N.
Tetrahedron
Lett.
2009,
50:
1533
9a
Cao H.
Jiang HF.
Qi CR.
Yao WJ.
Chen HJ.
Tetrahedron Lett.
2009,
50:
1209
9b
Liu WB.
Jiang HF.
Zhu SF.
Wang W.
Tetrahedron
2009,
65:
7985
9c
Jiang HF.
Li JH.
Chen ZW.
Tetrahedron
2010,
66:
9721
9d
Zhu Q.
Jiang HF.
Li J.
Liu S.
Xia C.
Zhang M.
J. Comb. Chem.
2009,
11:
685
10a
Sun J.
Xia EY.
Wu Q.
Yan CG.
Org.
Lett.
2010,
12:
3678
10b
Sun J.
Wu Q.
Xia EY.
Yan CG.
Eur. J. Org. Chem.
2011,
2981
10c
Sun J.
Xia EY.
Wu Q.
Yan CG.
ACS Comb. Sci.
2011,
13:
421
10d
Sun J.
Sun Y.
Xia EY.
Yan CG.
ACS Comb. Sci.
2011,
13:
436
11
Ghabraie E.
Balalaie S.
Bararjanian M.
Bijanzadeh HR.
Rominger F.
Tetrahedron
2011,
67:
5415
12
Gomez Sanchez A.
Mancera M.
Caballero FJ.
Bellanato J.
Anal.
Quim. Ser. C
1983,
79:
175 ; Chem. Abstr . 1985 , 102,
95485
13 Single crystal data for compounds 1d (CCDC 827899) and 1g (CCDC
827896) have been deposited at the Cambridge Crystallographic Data
Center. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or
from the Cambridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 (1223)336033,
E-mail: deposit@ccdc.cam.ac.uk].