Abstract
A highly efficient one-pot, two-step microwave-assisted procedure was applied for the rapid and green synthesis of benzo[a]phenazine annulated heterocyclic ring systems from the three- or four-component condensation reactions of 2-hydroxynaphthalene-1,4-dione, o-phenylenediamine, aromatic aldehydes and 1,3-indandione using L-proline as a bifunctional organocatalyst in water. This new procedure has a number of advantages such as high yields, very short reaction times, operational simplicity, simple work-up procedures and avoidance of hazardous or toxic catalysts and organic solvents. Moreover, the catalyst can be recovered and reused several times without much loss of its performance.
Keywords
References
1.
MacMillan D.W. C.
, Nature , 2008 , 455 , 304 .
2.
Dondoni A.
, and
Massi A.
, Angew. Chem., Int. Ed. , 2008 , 47 , 4638 .
3.
Yu X.H.
, and
Wang W.
, Asian J. Chem. , 2008 , 3 , 516 .
4.
Dalko P.I.
, and
Moisan L.
, Angew. Chem., Int. Ed. , 2004 , 43 , 5138 .
5.
Bertelsen S.
, and
Jorgensen K. A.
, Chem. Soc. Rev. , 2009 , 38 , 2178 .
6.
List B.
, Chem. Rev. , 2007 , 107 , 5413 .
7.
Mecadon H.
,
Rumum Md.
,
Kharbangar I.
,
Laloo B. M.
,
Kharkongor I.
,
Rajbangshi M.
, and
Myrboh B.
, Tetrahedron Lett. , 2011 , 52 , 3228 .
8.
Mukhopadhyay C.
,
Tapaswi P. K.
, and
Butcher R. J.
, Tetrahedron Lett. , 2010 , 51 , 1797 .
9.
Hernández J.G.
,
García-López V.
, and
Juaristi E.
, Tetrahedron , 2012 , 68 , 92 .
10.
Pandey J.
,
Anand N.
, and
Tripathi R. P.
, Tetrahedron , 2009 , 65 , 9350 .
11.
Shi C.
,
Chen H.
, and
Shi D.
, J. Heterocycl. Chem. , 2012 , 49 , 125 .
12.
Raghuvanshi D.S.
, and
Singh K. N.
, J. Heterocycl. Chem. , 2010 , 47 , 1323 .
13.
Hazeri N.
,
Maghsoodlou M. T.
,
Mir F.
,
Kangani M.
,
Saravani H.
, and
Molashahi E.
, Chin. J. Catal. , 2014 , 35 , 391 .
14.
Maghsoodlou M.T.
,
Hazeri N.
,
Lashkari M.
,
Shahrokhabadi F. N.
,
Naghshbandi B.
,
Kazemi-doost M. S.
,
Rashidi M.
,
Mir F.
,
Kangani M.
, and
Salahi S.
, Res. Chem. Intermed. , 2015 , 41 , 6985 .
15.
McNulty J.
, and
Das P.
, Eur. J. Org. Chem. , 2009 , 24 , 4031 .
16.
McNulty J.
,
Das P.
, and
McLeod D.
, Chem.–Eur. J. , 2010 , 16 , 6756 .
17.
Narayan S.
,
Muldoon J.
,
Finn M. G.
,
Fokin V. V.
,
Kolb H. C.
, and
Sharpless K. B.
, Angew. Chem., Int. Ed. , 2005 , 21 , 3157 .
18.
Smith M.B.
, and
March J.
, March's advanced organic chemistry , 6th edn. Wiley , Hoboken , 2007 .
19.
Breslow R.
, Organic reactions in water , ed.
Lindstrom M.
Blackwell , Oxford , 2007 , pp. 1 –28 .
20.
Breslow R.
, Acc. Chem. Res. , 1991 , 24 , 159 .
21.
Khanna G.
,
Chaudhary A.
, and
Khurana J. M.
, Tetrahedron Lett. , 2014 , 55 , 6652 .
22.
Jiang B.
,
Tu S. J.
,
Kaur P.
,
Wever W.
, and
Li G.
, J. Am. Chem. Soc. , 2009 , 131 , 11660 .
23.
Knapp J.M.
,
Zhu J. S.
,
Tantillo D. J.
, and
Kurth M. J.
, Angew., Chem. Int. Ed. , 2012 , 51 , 10588 .
24.
Li M.
,
Cao H.
,
Wang Y.
,
Lv X. L.
, and
Wen L. R.
, Org. Lett. , 2012 , 14 , 3470 .
25.
Khurana J.M.
,
Chaudhary A.
,
Lumb A.
, and
Nand B.
, Green Chem. , 2012 , 14 , 2321 .
26.
Bariwal J.B.
,
Trivedi J. C.
, and
Van der Eycken E. V.
, Top. Heterocycl. Chem. , 2010 , 25 , 169 .
27.
Garella D.
,
Borretto E.
,
Di Stilo A.
,
Martina K.
,
Cravotto G.
, and
Cintas P.
, MedChemComm , 2013 , 4 , 1323 .
28.
Das D.
,
Banerjee R.
, and
Mitra A.
, J. Chem. Pharm. Res. , 2014 , 6 (11 ), 108 .
29.
Chebanov V.A.
,
Muravyova E. A.
,
Desenko S. M.
,
Musatov V. I.
,
Knyazeva I. V.
,
Shishkina S. V.
,
Shishkin O. V.
, and
Kappe C. O.
, J. Comb. Chem. , 2006 , 8 , 427 .
30.
Laursen J.B.
, and
Nielsen J.
, Chem. Rev. , 2004 , 104 , 1663 .
31.
Price-Whelan A.
,
Dietrich L. E. P.
, and
Newman D. K.
, Nat. Chem. Biol. , 2006 , 2 , 71 .
32.
Mavrodi D.V.
,
Blankenfeldt W.
, and
Thomashow L. S.
, Annu. Rev. Phytopathol. , 2006 , 44 , 417 .
33.
Mavrodi D.V.
,
Peever T. L.
,
Mavrodi O. V.
,
Parejko J. A.
,
Raaijmakers J. M.
,
Lemanceau P.
,
Mazurier S.
,
Heide L.
,
Blankenfeldt W.
,
Weller D. M.
, and
Thomashow L. S.
, Appl. Environ. Microbiol. , 2010 , 76 , 866 .
34.
Lee H.J.
,
Kim J. S.
,
Park S. Y.
,
Suh M. E.
,
Kim H. J.
,
Seo E. K.
, and
Lee C. O.
, Bioorg. Med. Chem. , 2004 , 12 , 1623 .
35.
Kim J.S.
,
Rhee H.-K.
,
Park H. J.
,
Lee I.-K.
,
Lee S. K.
,
Suh M.-E.
,
Lee H. J.
,
Ryu C.-K.
, and
Park Choo H.-Y.
, Bioorg. Med. Chem. , 2007 , 15 , 451 .
36.
Mohebat R.
,
Yazdani-Elah-Abadi A.
,
Soltani A.
, and
Saghafi M.
, ARKIVOC , 2016 , iv , 1 .
37.
Mohebat R.
,
Yazdani-Elah-Abadi A.
, and
Maghsoodlou M.-T.
, Res. Chem. Intermed. , 2016 , 42 , 6039 .
38.
Yazdani-Elah-Abadi A.
,
Maghsoodlou M.-T.
,
Heydari R.
, and
Mohebat R.
, Res. Chem. Intermed. , 2016 , 42 , 1227 .
39.
Mohebat R.
,
Yazdani-Elah-Abadi A.
,
Maghsoodlou M.-T.
,
Mohammadi M.
, and
Heydari R.
, Res. Chem. Intermed. , 2016 , 42 , 7121 .
40.
Mohebat R.
,
Yazdani-Elah-Abadi A.
,
Maghsoodlou M.-T.
, and
Mohammadi M.
, Res. Chem. Intermed. , 2016 , 42 , 5915 .