Abstract
One-pot three-component condensation of aromatic ketones (1-tetralones, acetophenones, indane-1,3-dione), substituted aromatic aldehydes and thiourea in the presence of N-methylpyridinium tosylate under solvent free conditions at 100–110 °C for 2–4 h afforded tetrahydrobenzo[h]quinazoline-2-thiones, pyridimidine-2-thiones and indeno-pyrimidine-2-thiones in excellent yields. All synthesised thiones were screened for their antimicrobial activities.
References
1.
Pearce A.N.
,
Babcock R.C.
,
Battershill C.N.
,
Lambert G.
, and
Copp B.R.
, J. Org. Chem. , 2001 , 66 , 8257 .
2.
Shih D.H.
,
Baker F.
,
Cama L.
, and
Christensen B.G.
, Heterocycles , 1984 , 2 , 29 .
3.
Kelsey N.A.
,
Wilkins H.M.
, and
Linseman D.A.
, Molecules , 2010 , 15 , 7792 .
4.
Brown D.J.
, Quinazolines, Supplement I: The Chemistry of Heterocyclic Compounds , John Wiley & Sons , Chichester , 1996 . Vol. 55 .
5.
Witt A.
, and
Bergman J.
, Curr. Org. Chem. , 2003 , 7 , 659 .
6.
Michael J.P.
, Nat. Prod. Rep. , 2001 , 18 , 543 .
7.
Zhu S.
,
Wang J.
,
Chandrashekar G.
,
Smith E.
,
Liu X.
, and
Zhang Y.
, Eur. J. Med. Chem. , 2010 , 45 , 3864 .
8.
Kehler J.
,
Ritzen A.
,
Langgard M.
,
Petersen S.L.
,
Farah M.M.
,
Bundgaard C.
,
Christoffersen C.T.
,
Nielsen J.
, and
Kilburn J.P.
, Bioorg. Med. Chem. Lett. , 2011 , 21 , 3738 .
9.
Thanigaimalai P.
,
Sharma V.K.
,
Lee K.C.
,
Yun C.Y.
,
Kim Y.
, and
Jung S.H.
, Bioorg. Med. Chem. Lett. , 2010 , 20 , 4771 .
10.
Schleifer K.J.
, J. Med. Chem. , 1999 , 42 , 2204 .
11.
Zorkun I.S.
,
Saraç S.
,
Celebi S.
, and
Erol K.
, Bioorg. Med. Chem. , 2006 , 14 , 8582 .
12.
Mishra R.
,
Mishra B.
, and
Moorthy N.S.H.N.
, Trends in Appl. Sci. Res. , 2008 , 3 , 203 .
13.
Tale R.H.
,
Rodge A.H.
,
Hatnapure G.D.
, and
Keche A.P.
, Bioorg. Med. Chem. Lett. , 2011 , 21 , 4648 .
14.
Sayed H.H.
,
Abbas H.A.S.
,
Amr A.G.E.
, and
Abdelwahad N.A.M.
, Acta. Pharm. , 2010 , 60 , 479 .
15.
El-Zahar M.I.
,
El-karim S.S.A.
,
Haiba M.E.
, and
Khedr M.A.
, Acta. Pol. Pharm. , 2011 , 68 (3 ), 357 .
16.
Pal R.
,
Handa R.N.
, and
Pujari H.K.
, Indian J. Chem. , 1993 , 32B , 929 .
17.
Kaur B.
, and
Kaur R.
, ARKIVOC , 2007 , (xv ), 315 .
18.
Safaei-Ghomi J.
, and
Ghasemzadeh M.A.
, J. Serb. Chem. Soc. , 2011 , 76 (5 ), 679 .
19.
Shen Z.L.
,
Xu X.P.
, and
Ji S.J.
, J. Org. Chem. , 2010 , 75 , 1162 .
20.
Zhu Y.
,
Huang S.
,
Wan J.
,
Yan L.
,
Pan Y.
, and
Wu A.
, Org. Lett. , 2006 , 8 , 2599 .
21.
Kroutil J.
, and
Budesinsky M.
, Carbohydr. Res. , 2007 , 342 , 147 .
22.
Arthington-Skaggs B.A.
,
Motley M.
,
Warnock D.W.
, and
Morrison C.J.
, J. Clin. Microbiol. , 2000 , 38 , 2254 .
23.
Pal R.
,
Handa R.N.
, and
Pujari H.K.
, Indian J. Chem. , 1994 , 33B , 629 .
24.
Gupta R.
, and
Chaudhary R.P.
, Phosphorus, Sulfur, Silicon Relat. Elem. , 2012 , 187 , 735 .
25.
Gupta R.
, and
Chaudhary R.P.
, Asian J. Chem. , 2012 , 24 (5 ), 2113 .
26.
Phucho I.T.
,
Nongpiur A.
,
Nongrum R.
, and
Nongkhlaw R.L.
, Indian J. Chem. , 2010 , 49B , 346 .