Abstract
A new and convenient method is describe d for the synthesis of 3-aryl-benzo[b]furans and 3-aryl-naphtho[b]furans by the reaction of various α-bromoketones with phenols and 2-naphthols in the presence of n-propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride immobilised on SiO2. All products were obtained in high yields and short reaction times using solvent-free conditions and a reusable catalyst.
References
1.
Hiremathad A.
,
Patil M.R.
,
Chethana K.R.
,
Chand K.
,
Santos M.A.
and
Keri R.S.
, RSC Adv. , 2015 , 5 , 96809 .
2.
Khanam H.
, Eur. J. Med. Chem. , 2015 , 97 , 483 .
3.
Asif M.
, J. Anal. Pharm. Res. , 2016 , 3 , 00050 .
4.
Xia L.
,
Idhayadhulla A.
,
Lee Y.R.
,
Kim S.H.
and
Wee Y.-J.
, Med. Chem. Res. , 2014 , 23 , 3528 .
5.
Salmon R.
,
Buisson J.
,
Zafrani B.
,
Aussepe L.
and
Royer R.
, Carcinogenesis , 1986 , 7 , 1447 .
6.
Srivastava V.
,
Negi A.S.
,
Kumar J.K.
,
Faridi U.
,
Sisodia B.S.
,
Darokar M.P.
,
Luqman S.
and
Khanuja S.P.S.
, Bioorg. Med. Chem. Lett. , 2006 , 16 , 911 .
7.
Gan C.-S.
,
Nan D.-D.
,
Qiao J.-P.
,
Wang C.-W.
and
Zhou J.-N.
, J. Nucl. Med. , 2012 , 53 , 1620 .
8.
Heravi M.M.
and
Zadsirjan V.
, Adv. Heterocycl. Chem. , 2015 , 117 , 261 .
9.
Heravi M.M.
,
Zadsirjan V.
,
Hamidi H.
and
Amiri P.H.T.
, RSC Adv. , 2017 , 7 , 24470 .
10.
Tharra P.
, and
Baire B.
, Chem. Commun. , 2016 , 52 , 14290 .
11.
Lingam V.P.R.
,
Dahale D.H.
,
Mukkanti K.
,
Gopalan B.
and
Thomas A.
, Tetrahedron Lett. , 2012 , 53 , 5695 .
12.
Lee J.H.
,
Kim M.
, and
Kim I.
, J. Org. Chem. , 2014 , 79 , 6153 .
13.
Moure M.J.
,
SanMartin R.
and
Dominguez E.
, Angew. Chem. Int. Ed. , 2012 , 51 , 3220 .
14.
Sakiyama N.
,
Noguchi K.
and
Tanaka K.
, Angew. Chem. Int. Ed. , 2012 , 51 , 5976 .
15.
Huo C.
,
An J.
,
Xu X.
,
Jia X.
,
Wang X.
and
Kang L.
, Tetrahedron Lett. , 2013 , 54 , 1145 .
16.
Sonogashira K.
,
Tohda Y.
and
Hagihara N.
, Tetrahedron Lett. , 1975 , 16 , 4467 .
17.
Jindal R.
and
Surya A.S.
, Curr. Green Chem. , 2015 , 2 , 135 .
18.
Vekariya R.L.
, J. Mol. Liq. , 2017 , 227 , 44 .
19.
Hasaninejad A.
,
Shekouhy M.
,
Golzar N.
,
Zare A.
and
Doroodmand M.M.
, Appl. Cat. A , 2011 , 402 , 11 .
20.
Rigi F.
and
Shaterian H.R.
, Polycycl. Aromat. Compd , 2017 , 37 , 314 .
21.
Wang B.
,
Hu J.
,
Zhang F.
and
Zheng H.
, Heterocycles , 2016 , 92 , 103 .
22.
Scherrer R.A.
,
Stern R.M.
,
Hammar W.J.
and
Walton J.H.
, U.S. Patent: US4526896 A, issued 2 July 1985 .
23.
Vasquez-Cespedes S.
,
Chepiga K.M.
,
Möller N.
,
Schafer A.H.
and
Glorius F.
ACS Catal. , 2016 , 6 , 5954 .
24.
Liu G.
and
Lu X.
Tetrahedron , 2008 , 64 , 7324 .
25.
Wang B.
,
Zhang J.
,
Liao J.
,
Peng Y.
and
Zheng H.
, Heterocycles , 2016 , 92 , 1468 .
26.
Chen Z.
,
Wang X.
,
Lu W.
and
Yu J.
Synlett , 1991 , 1991 , 121 .
