Abstract
An eco-friendly and efficient straightforward method has been developed for the synthesis of ethyl 3-amino-1-aryl-1H-benzo[f]chromene-2-carboxylate derivatives via 1,4-diazabicyclo[2.2.2]octane (DABCO)-catalysed cyclisation of β-naphthol and 3-aryl-2-cyanoacrylates using water as a green solvent. All products precipitated from the reaction mixture and were isolated by simple filtration. No further work-up nor purification was necessary. The structure of ethyl 3-amino-1-aryl-1H-benzo[f]chromene-2-carboxylate was further confirmed by X-ray single crystal analysis.
References
1.
Jamison J.M.
,
Krabill K.
, and
Hatwalkar A.
, Cell Biol. Int. Rep. , 1990 , 14 , 1075 .
2.
Smith W.P.
,
Sollis L. S.
,
Howes D. P.
,
Cherry C. P.
,
Starkey D. I.
, and
Cobley N. K.
, J. Med. Chem. , 1998 , 41 , 787 .
3.
Mirjalili B.F.
,
Zamani L.
,
Zomorodian K.
,
Khabnadideh S.
,
Haghighijoo Z.
,
Malakotikhah Z.
,
Mousavi S. A. A.
, and
Khojasteh S.
, J. Mol. Structure , 2016 , 1116 , 102 .
4.
Khafagy M.M.
,
El-Wahas A. H. F. A.
,
Eid F. A.
, and
El-Agrody A. M.
, Farmaco , 2002 , 57 , 715 .
5.
Dgachi Y.
,
Bautista-Aguilera O. M.
,
Benchekroun M.
,
Martin H.
,
Bonet A.
,
Knez D.
,
Godyn J.
,
Malawska B.
,
Gobec S.
,
Chioua M.
,
Janockova J.
,
Soukup O.
,
Chabchoub F.
,
Marco-Contelles J.
, and
Ismaili L.
, Molecules , 2016 , 21 , 634 .
6.
Mohr S.J.
,
Chirigos M. A.
,
Fuhrman F. S.
, and
Pryor J. W.
, Cancer Res. , 1975 , 35 , 3750 .
7.
Bianchi G.
, and
Tava A.
, Agric. Biol. Chem. , 1987 , 51 , 2001 .
8.
Eiden F.
, and
Denk F.
, Arch. Pharm. , 1991 , 324 , 353 .
9.
Poupelin J.P.
,
Saint-Ruf G.
,
Foussard-Blanpin O.
,
Narcisse G.
,
Uchida-Emouf G.
, and
Lacroix R.
, Eur. J. Med. Chem. , 1978 , 13 , 67 .
10.
Bhowmik B.B.
, and
Ganguly P.
, Spectrochim. Acta A , 2005 , 61 , 1997 .
11.
Sirkecioglu O.
,
Talinli N.
, and
Akar A.
, J. Chem. Res. (S) , 1995 , 502 .
12.
Mkaouar K.
,
Chabchoub F.
,
Samadi A.
,
Contelles J. L. M.
, and
Salem M.
, Synth. Commun. , 2010 , 40 , 3405 .
13.
Ren Y.M.
, and
Cai C.
, Catal. Commun. , 2008 , 9 , 1017 .
14.
Sabitha G.
,
Bhikshapathi M.
,
Nayak S.
,
Srinivas R.
, and
Yadav J. S.
, J. Heterocycl. Chem. , 2011 , 48 , 267 .
15.
Kiyani H.
, and
Ghorbani F.
, Res. Chem. Intermed. , 2015 , 41 , 7847 .
16.
Balalaie S.
,
Ramezanpour S.
,
Bararjanian M.
, and
Gross J. H.
, Synth. Commun. , 2008 , 38 , 1078 .
17.
Paplal B.
,
Nagaraju S.
,
Veerabhadraiah P.
,
Sujatha K.
,
Kanvah S.
,
Kumar B. V.
, and
Kashinath D.
, RSC Adv. , 2014 , 4 , 54168 .
18.
Moghanian H.
,
Mobinikhaledi A.
, and
Deinavizadeh M.
, Res. Chem. Intermed. , 2015 , 41 , 4387 .
19.
Bob E.
,
Hillringhaus T.
,
Nitsch J.
, and
Klussmann M.
, Org. Biomol. Chem. , 2011 , 9 , 1744 .
20.
van Otterlo W.A. L.
,
Ngidi E. L.
,
Kuzvidza S.
,
Morgans G. L.
,
Moleele S. S.
, and
de Koning C. B.
, Tetrahedron , 2005 , 61 , 9996 .
21.
Nishibayashi Y.
,
Inada Y.
,
Hidai M.
, and
Uemura S.
, J. Am. Chem. Soc. , 2002 , 124 , 7900 .
22.
Rousseaux S.
,
Liegault B.
, and
Fagnoux K.
, Chem. Sci. , 2012 , 3 , 244 .
23.
Fan X.
,
Wang Y.
,
Qu Y.
,
Xu H.
,
He Y.
,
Zhang X.
, and
Wang J.
, J. Org. Chem. , 2011 , 76 , 982 .
24.
Tang J.
,
Zhao S.
,
Wei Y.
,
Quan Z.
, and
Huo C.
, Org. Biomol. Chem. , 2017 , 15 , 1589 .
25.
Fujiwara M.
,
Sakamoto M.
,
Komeyama K.
,
Yoshida H.
, and
Takaki K.
, J. Heterocycl. Chem. , 2015 , 52 , 59 .
26.
Aït-Baziz N.
,
Hamdi S. M.
,
Silva A. M. S.
,
Rachedi Y.
,
Hamdi M.
, and
Trarie M.
, J. Heterocycl. Chem. , 2014 , 51 , 1240 .
27.
Amatore C.
,
Le Duc G.
, and
Jutand A.
, Chem. Eur. J. , 2013 , 19 , 10082 .
28.
Simon M.O.
, and
Li C. J.
, Chem. Soc. Rev. , 2012 , 41 , 1415 .
29.
Zhang J.
,
Yao J.
,
Liu J.
,
Xue S.
,
Li Y.
, and
Wang C.
, RSC Adv. , 2015 , 5 , 48580 .
30.
Bian X.
,
Wang L.
,
Liu J.
, and
Wang C.
, J. Chem. Res. , 2016 , 40 , 289 .
31.
Lu C.
, Chinese J. Chem. , 2010 , 28 , 2469 .
32.
Zhuang Q.
,
Shi D.
, and
Wang X.
, Acta Crystallogr., Sect. E: Struct. Rep. Online , 2003 , 59 , o1474 .