Abstract
The 1,3-dipolar cycloaddition reaction of (Z)-5-arylidene[1,3]thiazolo[3,2-b][1,2,4]triazol-6(5H)-one and azomethine ylide, which was generated in situ by the reaction of N-4-methoxyphenacylbenzothiazolium bromides and triethylamine, afforded novel 2-(aryl)-1-(4-methoxybenzoyl)-1,2-dihydrospiro[pyrrolo[2,1-b][1,3]benzothiazole-3,5′-[1,3]thiazolo[3,2-b][1,2,4]triazol]-6′-ones in moderate yields. The structures of all the products were characterised thoroughly by NMR, IR and HRMS spectroscopy together with X-ray crystallographic analysis.
Keywords
References
1.
Pignatello R.
,
Mazzone S.
,
Panico A.M.
,
Mazzone G.
,
Pennisi G.
,
Castana R.
,
Matera M.
, and
Blandino G.
, Eur. J. Med. Chem. , 1991 , 26 , 929 .
2.
Aktay G.
,
Tozkoparan B.
, and
Ertan M.
, J. Enzym. Inhib. Med. Chem. , 2009 , 24 , 898 .
3.
Sarigol D.
,
Uzgoren-Baran A.
,
Tel B.C.
,
Somuncuoglu E.I.
,
Kazkayasi I.
,
Ozadali-Sari K.
,
Unsal-Tan O.
,
Okay G.
,
Ertan M.
, and
Tozkoparan B.
, Bioorg. Med. Chem. , 2015 , 23 , 2518 .
4.
Baran A.U.
,
Tel B.C.
,
Sarigöl D.
,
Öztürk E.I.
,
Kazkayasi I.
,
Okay G.
,
Ertan M.
, and
Tozkoparan B.
, Eur. J. Med. Chem. , 2012 , 57 , 398 .
5.
Wan Y.C.
,
Dai N.N.
,
Tang Z.L.
, and
Fang H.
, Eur. J. Med. Chem. , 2018 , 146 , 471 .
6.
Trost B.M.
, and
Brennan M.K.
, Synthesis , 2009 , 18 , 3003 .
7.
Cravotto G.
,
Giovenzana G.B.
,
Pilot T.
,
Sisti M.
, and
Palmisano M.
, J. Org. Chem. , 2001 , 66 , 8447 .
8.
Girgis A.S.
, Eur. J. Med. Chem. , 2009 , 44 , 1257 .
9.
Girgis A.S.
, Eur. J. Med. Chem. , 2009 , 44 , 91 .
10.
Lakshmi N.V.
,
Thirumurugan P.
, and
Perumal P.T.
, Tetrahedron Lett. , 2010 , 51 , 1064 .
11.
Jin G.
,
Sun J.
,
Yang R.Y.
, and
Yan C.G.
, Sci. Rep. , 2017 , 7 , 46470 .
12.
Jiang W.
,
Sun J.
, and
Yan C.G.
, RSC Adv. , 2017 , 7 , 42387 .
13.
Shen G.L.
,
Sun J.
, and
Yan C.G.
, Org. Biomol. Chem. , 2015 , 13 , 10929 .
14.
Li X.F.
,
Liu B.
,
Yu X.Y.
,
Yi P.G.
,
Yi R.Q.
, and
Chmielewski P.J.
, J. Org. Chem. , 2012 , 77 , 2431 .
15.
Fu X.L.
,
Meng Y.K.
,
Li X.F.
,
Stępień M.
, and
Chmielewski P.J.
, Chem. Commun. , 2018 , 54 , 2510 .
16.
Liu B.
,
Li X.F.
,
Liu H.
, and
Yu X.
, Tetrahedron Lett. , 2013 , 54 , 6952 .
17.
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 .
18.
Zhang S.W.
,
Ren D.M.
,
Hu X.L.
,
Fu X.L.
, and
Li X.F.
, J. Chem. Res. , 2017 , 41 , 641 .
