Abstract
Aryl glyoxals reacted with malononitrile and 4-hydroxycoumarin in the presence of a catalytic amount of TiO2 nanoparticles to give a hitherto unknown family of pyranochromenes in up to 80% yield. This new three-component reaction yielded some novel pyrano[3,2-c]chromene-5-ones containing an aroyl substituent. Using a recyclable and safe catalyst along with a green solvent system made the process eco-friendly and economic.
References
1.
Karami B.
,
Ferdosian R.
, and
Eskandari K.
, J. Chem. Res. , 2014 , 38 , 41 .
2.
Gu Y.
, Green Chem. , 2012 , 14 , 2091 .
3.
Karami B.
,
Eskandari K.
, and
Khodabakhshi S.
, J. Iran. Chem. Soc. , 2014 , 11 , 631 .
4.
Lee H.-I.
,
Lee J.-H.
,
Park K.-H.
,
Sangurdekar D.
, and
Chang W.-S.
, Appl. Environ. Microbiol. , 2012 , 78 , 2896 .
5.
Martins S.M.A.
,
Branco P.C.S.
, and
Pereira A.M.D.R.L.
, J. Braz. Chem. Soc. , 2012 , 23 , 688 .
6.
Karami B.
,
Eskandari K.
, and
Khodabakhshi S.
, Arkivoc , 2012 , (ix ), 76 .
7.
Karami B.
,
Khodabakhshi S.
, and
Eskandari K.
, Tetrahedron Lett. , 2012 , 53 , 1445 .
8.
Sagar R.
,
Park J.
,
Koh M.
, and
Park S.B.
, J. Org. Chem. , 2009 , 74 , 2171 .
9.
Evans J.M.
,
Fake C.S.
,
Hamilton T.C.
,
Poyser R.H.
, and
Showell G.A.
, J. Med. Chem. , 1984 , 27 , 1127 .
10.
Ziarani G.M.
, and
Hajiabbasi P.
, Heterocycles , 2013 , 87 , 1415 .
11.
Ghorbani-Vaghei R.
,
Toghraei-Semiromi Z.
, and
Karimi-Nami R.
, J. Braz. Chem. Soc. , 2011 , 22 , 905 .
12.
Dmitriev M.V.
,
Silaichev P.S.
, and
Maslivets A.N.
, Russ. J. Org. Chem. , 2011 , 47 , 1263 .
13.
Khan A.T.
,
Lal M.
,
Ali S.
, and
Khan Md. M.
, Tetrahedron Lett. , 2011 , 52 , 5327 .
14.
Pansuriya A.M.
,
Savant M.M.
,
Bhuva C.V.
,
Singh J.
, and
Naliapara Y.T.
, Arkivoc , 2009 , (xii ), 254 .
15.
Alinezhad H.
,
Tajbakhsh M.
,
Salehian F.
, and
Biparva P.
, Bull. Korean Chem. Soc. , 2011 , 32 , 3720 .
16.
Shirini F.
,
Atghia S.V.
, and
Alipour Khoshdel M.
, Iran. J. Catal. , 2011 , 1 , 93 .
17.
Mirjalili B.B.F.
, and
Akbari A.
, Z. Naturforsch. , 2009 , 64b , 347 .
18.
Karami B.
,
Khodabakhshi S.
, and
Nikrooz N.
, Polycyclic Aromat. Compd. , 2011 , 31 , 97 .
19.
Khodabakhshi S.
,
Karami B.
, and
Eskandari K.
, C. R. Chimie , 2014 , 17 , 35 .