Abstract
An efficient and convenient synthesis of new thiazino[2,3-b]quinoxaline derivatives has been developed by employing a one-pot cyclo-condensation of several α-haloketones and 3-aminoquinoxaline-2-thiol in acetic acid. A similar reaction with 4-bromo-3-methyl-4,5-dihydro-1H-5-pyrazolone gave a new heterocyclic system, 3-methyl-1,4-dihydropyrazolo[4′,3′:5,6][1,4] thiazino[2,3-b]quinoxaline.
References
1.
Amin M.A.
, and
Youssef M.M.
, Org. Chem.: Indian J. , 2013 , 9 , 1323 .
2.
Khan S.A.
,
Saleem K.
, and
Khan Z.
, Eur. J. Med. Chem. , 2007 , 42 , 103 .
3.
Tandon V.K.
,
Yadava D.B.
,
Maurya A.K.
, and
Shukla P.K.
, Bioorgan. Med. Chem. , 2008 , 14 , 6120 .
4.
Abu-Hashem A.A.
,
Gouda M.A.
, and
Badria F.A.
, Eur. J. Med. Chem. , 2010 , 45 , 1976 .
5.
Islami M.R.
, and
Hassani Z.
, Arkivoc , 2008 , 15 , 208 .
6.
Srinivas Ch.
,
Sai Pavan Kumar Ch. N.S.
,
Jayathirtha Rao V.
, and
Palaniappan S.
, Catal. Lett. , 2008 , 121 , 291 .
7.
Bachhav M.H.
,
Bhagat S.B.
, and
Telvekar V.N.
, Tetrahedron Lett. , 2011 , 52 , 5697 .
8.
Ali I.A.
,
Al-Masoudi I.A.
,
Hassan H. Gh.
, and
Al-Masoudi N.A.
, Chem. Heterocycl. Compd. , 2007 , 43 , 1052 .
9.
Gazit A.
,
Yee K.
,
Uecker A.
,
Böhmer C.F.
,
Sjöblom T.
,
Östman A.
,
Waltenberger J.
,
Golomb G.
,
Banai Sh.
,
Heinrich M.
, and
Levitzki A.
, Bioorgan. Med. Chem. , 2003 , 11 , 2007 .
10.
Schwarz S.
,
Kehrenberg C.
, and
Walsh T.R.
, Int. J. Antimicrob. Agents , 2001 , 17 , 431 .
11.
Heravi M.M.
,
Bakhtiari Kh.
,
Bamoharram F.
, and
Tehrani M.H.
, Monatsh. Chem. , 2007 , 138 , 465 .
12.
Kumar A.
,
Saxena A.
,
De A.
, and
Mozumdar S.
, Catal. Commun. , 2008 , 9 , 778 .
13.
Justin Thomas K.R.
,
Velusamy M.
,
Lin J.
,
Chuen Ch.
, and
Tao Y.
, Chem. Mater. , 2005 , 17 , 1860 .
14.
Yamashita Y.
, Sci. Technol. Adv. Mater. , 2009 , 10 , 024313 .
15.
Meshram H.M.
,
Santosh Kumar G.
,
Ramesh P.
, and
Chennakesava Reddy B.
, Tetrahedron Lett. , 2010 , 51 , 2580 .
16.
Heravi M.M.
,
Baghernejad B.
, and
Oskooie H.
, Tetrahedron Lett. , 2009 , 50 , 767 .
17.
Castro P.P.
,
Zhao G.
,
Masangkay G.A.
,
Hernandez C.
, and
Gutierrez-Tunstad L.M.
, Org. Lett. , 2004 , 6 , 333 .
18.
Aravind K.
,
Ganesh A.
, and
Ashok D.
, J. Chem. Pharm. Res. , 2013 , 5 , 48 .
19.
Haldar P.
,
Dutta B.
,
Guin J.
, and
Ray J.K.
, Tetrahedron Lett. , 2007 , 48 , 5855 .
20.
Zhou J.
,
Gong G.
,
An L.
,
Liu Y.
,
Zhu F.
,
Zhu Y.
, and
Ji Sh.
, Synlett , 2008 , 20 , 3163 .
21.
Aparicio D.
,
Attanasi O.A.
,
Filippone P.
,
Ignacio R.
,
Lillini S.
,
Mantellini F.
,
Palacios F.
, and
de los Santos J.M.
, J. Org. Chem. , 2006 , 71 , 5897 .
22.
Singh S.K.
,
Gupta P.
,
Duggineni S.
, and
Kundu B.
, Synlett , 2003 , 14 , 2147 .
23.
Panneerselvam P.
,
Reddy R.S.
,
Murali K.
, and
Kumar N.R.
, Der Pharma Chem. , 2010 , 2 , 28 .
24.
Mazumdera J.
,
Chakraborty R.
,
Sena S.
,
Vadrab S.
,
Dec B.
, and
Ravi T.K.
, Der Pharma Chem. , 2009 , 2 , 188 .
25.
Wolf-Diethard P.
,
Annemarie H.
,
Pavel P.
,
Anja B.
, and
Jana M.
, J. Heterocycl. chem. , 1999 , 36 , 1327 .
26.
Sonawane Y.A.
,
Rajule R.N.
, and
Shankarling G.S.
, Monatsh. Chem. , 2010 , 141 , 1145 .