Abstract
An efficient strategy for the preparation of a novel structural variant of imidazoquinazolines with three-point diversity has been described. The compounds were obtained by treating benzil with o -nitrobenzaldehyde to give imidazoles, followed by reduction of the nitro group to give an aryl amine. Condensation-cyclization of the resulting intermediate with isothiocyanates in the presence of DBU for 45 minutes at room temperature furnished the title compounds in high yields and purities.
Key words
imidazoquinazoline - imidazole - DBU
References 1 CDRI Communication No. 6900.
2
Mannschreck A.
Koller H.
Stuhler G.
Davies MA.
Traber J.
Eur. J. Med. Chem.
1984,
19:
381
3
Molamas MS.
Miller J.
J. Med. Chem.
1991,
34:
1492
4
Spence CM.
Bergden RN.
Drugs
1994,
47:
809
5
Venuti MC.
Stephenson RA.
Alvarez R.
Bruno JJ.
Strosberg AM.
J. Med. Chem.
1988,
31:
2136
6 Kundu, B. presented at IUPAC-BNP-2004, New Delhi, India, 26th-31st January 2004.
7
Gueiffier A.
Mavel S.
Lhassani M.
Elhakmaoui A.
Snoeck R.
Andrei G.
Chavignon O.
Teulade JC.
Witvrouw M.
Balzarini J.
Clercq EDC.
J. Med. Chem.
1998,
41:
5108
8a
Kesarwani AP.
Grover R.
Roy R.
Kundu B.
Tetrahedron
2005,
61:
629
8b
Srivastava GK.
Kesarwani AP.
Grover RK.
Srinivasan T.
Roy R.
Kundu B.
J. Comb. Chem.
2003,
5:
769
8c
Grover R.
Kesarwani AP.
Srivastava GK.
Kundu B.
Roy R.
Tetrahedron
2005,
61:
5011
9
Perron D.
Conlon D.
Bousquet PF.
Robinson SP.
J. Heterocycl. Chem.
1997,
34:
807
10a
Molina P.
Alajarin M.
Vidal A.
Tetrahedron Lett.
1988,
29:
3849
10b
Molina P.
Alajarin M.
Vidal A.
Tetrahedron
1989,
45:
4263
11
Krieg B.
Manecke G.
Z. Naturforsch., B
1967,
22:
132
12a
Krchank V.
Smith J.
Vagner J.
Tetrahedron Lett.
2001,
42:
1627
12b
Smith J.
Liras J.
Schneider SE.
Anslyn EV.
J. Org. Chem.
1996,
61:
8811
12c
Li M.
Wilson J.
Protlock DE.
Tetrahedron Lett.
2001,
42:
2273
12d
Song A.
Marik J.
Lam KS.
Tetrahedron Lett.
2004,
45:
2727
13
Wang JX.
Zhang L.
Xu Y.
Krishnamurthy D.
Sananayake CH.
Tetrahedron Lett.
2004,
45:
7167