Abstract
The 1,3-dipolar cycloaddition reaction of ethyl-5-aryl-2-[(Z)-2-methoxy-2-oxoethylidene]-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a] pyrimidine-6-carboxylates and azomethine ylide, which was generated in situ by the reaction of N-4-methoxyphenacylbenzothiazolium bromides and triethylamine, yielded novel 6′-ethyl-2-methyl-5′-aryl-1-(4-methoxybenzoyl)-7-methyl-3′-oxo-1,2-dihydro-5H-spiro[pyrrolo[2,1-b][1,3]benzothiazole-3,2′-[1,3]thiazolo[3,2-a]pyrimidine]-2,6′-dicarboxylates in moderate yields. The structures of all of the products were characterised by NMR, IR, HRMS spectrometry, together with X-ray crystallographic analysis.
Keywords
References
1.
Trost B.M.
, and
Brennan M.K.
, Synthesis , 2009 , 18 , 3003 .
2.
Cravotto G.
,
Giovenzana G.B.
,
Pilot T.
,
Sisti M.
, and
Palmisano M.
, J. Org. Chem. , 2001 , 66 , 8447 .
3.
Girgis A.S.
, Eur. J. Med. Chem. , 2009 , 44 , 1257 .
4.
Girgis A.S.
, Eur. J. Med. Chem. , 2009 , 44 , 91 .
5.
Lakshmi N.V.
,
Thirumurugan P.
, and
Perumal P.T.
, Tetrahedron Lett. , 2010 , 51 , 1064 .
6.
Sridhar G.
,
Gunasundari T.
, and
Raghunathan R.
, Tetrahedron Lett. , 2007 , 48 , 319 .
7.
Periyasami G.
,
Raghunathan R.
,
Surendiran G.
, and
Mathivanan N.
, Eur. J. Med. Chem. , 2009 , 44 , 959 .
8.
Jin G.
,
Sun J.
,
Yang R.Y.
, and
Yan C.G.
, Sci. Rep. , 2017 , 7 , 46470 .
9.
Jiang W.
,
Sun J.
, and
Yan C.G.
, RSC Adv. , 2017 , 7 , 42387 .
10.
Shen G.L.
,
Sun J.
, and
Yan C.G.
, Org. Biomol. Chem. , 2015 , 13 , 10929 .
11.
Back T.
,
Prado R.
,
Zhao W.Z.
,
Watson B.D.
, and
Ginsberg M.D.
, Neurol. Res. , 1998 , 20 , 643 .
12.
Russo F.
,
Guccione S.
,
Romeo G.
,
Barretta G.U.
,
Pucci S.
,
Caruso A.
,
Roxas M.A.
, and
Cutuli V.
, Eur. J. Med. Chem. , 1993 , 28 , 363 .
13.
Ghorab M.M.
,
Mohamad Y.A.
,
Mohamed S.A.
, and
Ammar Y.A.
, Phosphorus, Sulfur Silicon Relat. Elem. , 1996 , 108 , 249 .
14.
Tozkoparan B.
,
Ertan M.
,
Kelicen P.
, and
Demirdamar R.
, Farmaco , 1999 , 54 , 588 .
15.
Duval R.
,
Kolb S.
,
Braud E.
,
Genest D.
, and
Garbay C.
, J. Comb. Chem. , 2009 , 11 , 947 .
16.
Li X.F.
,
Liu B.
,
Yu X.Y.
,
Yi P.G.
,
Yi R.Q.
, and
Chmielewski P.J.
, J. Org. Chem. , 2012 , 77 , 2431 .
17.
Fu X.L.
,
Meng Y.K.
,
Li X.F.
,
St pie M.
, and
Chmielewski P.J.
, Chem. Commun. , 2018 , 54 , 2510 .
18.
Liu B.
,
Li X.F.
,
Liu H.C.
, and
Yu X.Y.
, Tetrahedron Lett. , 2013 , 54 , 6952 .
19.
Liu B.
,
Cong H.L.
,
Li X.F.
,
Yu B.
,
Bao L.P.
,
Cai W.T.
,
Xie Y.P.
, and
Lu X.
, Chem. Commun. , 2014 , 50 , 12710 .
20.
Zeng R.J.
,
Zhou Z.C.
,
Wang Z.X.
,
Li X.F.
,
Chen Z.
, and
Yu X.Y.
, Chin. J. Org. Chem. , 2009 , 29 , 470 .