Abstract
A distinct approach for the synthesis of 1,3,3-trisubstituted
4,5-dioxopyrrolidines and 1,3,4,5-tetrasubstituted 1,2,3,6-tetrahydropyrimidines
has been discovered, in the form of a three-component reaction of
nitroarenes, formaldehyde, and dialkyl acetylenedicarboxylates using
indium in dilute aqueous HCl at room temperature. The molar ratios
of these substrates are 1:1:4 and 2:1:4 for the preparation of dioxopyrrolidines
and tetrahydropyrimidines, respectively. The reactions involve the
reduction of nitro compounds to amines, which are simultaneously
attacked by dialkyl acetylenedicarboxylates and formaldehyde. The
products are formed in good to high yields.
Key words
pyrrolidines - tetrahydropyrimidines - nitro
compounds - multicomponent synthesis - reactions
in water
References
1 Part 202 in the series: ‘Studies
on Novel Synthetic Methodologies’.
2a
Janecki T.
Blaszczyk E.
Studzian K.
Janecka A.
Krajenska U.
Rozalski M.
J.
Med. Chem.
2005,
48:
3516
2b
Hong CY.
Kim YK.
Chang JH.
Kim SH.
Choi H.
Nam DH.
Kim YZ.
Kwak JH.
J.
Med. Chem.
1997,
40:
3584
2c
Raj AA.
Raghunathan R.
Sridevi Kumari MR.
Raman N.
Bioorg.
Med. Chem.
2003,
11:
407
3a
Nair V.
Chi G.
Ptak R.
Neamati N.
J. Med.
Chem.
2006,
49:
445
3b
Pattarimi P.
Smeyne RJ.
Morgan JI.
Neuroscience
2007,
145:
654
3c
Messer WS.
Abuh YF.
Paryasamy S.
Ngur DO.
Edger MAN.
Eissadi AA.
Sheih S.
Dunbar PG.
Roknich S.
Rho T.
Fang Z.
Ojo B.
Zhang H.
Huzl JJ.
Nagy PI.
J. Med. Chem.
1997,
40:
1230
4
Tozkoparan B.
Yarim M.
Sarac S.
Ertan M.
Kelicun P.
Altinoc G.
Demirdamar R.
Arch.
Pharm. Pharm. Med. Chem.
2000,
333:
415
For recent examples of multicomponent
reactions, see:
5a
Ohno H.
Ohta Y.
Oishi S.
Fujii N.
Angew. Chem. Int. Ed.
2007,
46:
2295
5b
Komagawa S.
Saito S.
Angew. Chem. Int. Ed.
2006,
45:
2446
5c
Yoshida H.
Fukushima H.
Ohshita J.
Kunai A.
J. Am. Chem. Soc.
2006,
128:
11040
5d
Dondas H.
Fishwick CWG.
Gai X.
Grigg R.
Kilner C.
Dumrongchai N.
Kongkathip B.
Kongkathip N.
Polysuk C.
Sridharan V.
Angew. Chem. Int. Ed.
2005,
44:
7570
5e
Pache S.
Lautens M.
Org. Lett.
2003,
5:
4827
6a
Cao H.
Jiang H.-F.
Qi C.-R.
Yao W.-J.
Chem H.-J.
Tetrahedron Lett.
2009,
50:
1209
6b Srikrishna A., Sridharan
M., Prasad K. R.; Tetrahedron; 2010, 66: in
press; DOI: 10.1016/ j.tet.2010.03.084
7a
Das B.
Banerjee J.
Mahender G.
Majhi A.
Org. Lett.
2004,
6:
3349
7b
Das B.
Holla H.
Venkateswalu K.
Majhi A.
Tetrahedron Lett.
2005,
46:
8895
7c
Das B.
Satyalakshmi G.
Suneel K.
Shashikanth B.
Tetrahedron Lett.
2008,
49:
7209
8
Ranu BC.
Eur.
J. Org. Chem.
2000,
2347
9
Lee JC.
Choi KII.
Koh HY.
Kang Y.
Kuin Y.
Kang Y.
Cho YS.
Synthesis
2001,
81
