Abstract
3-(Naphlhyl-1-amino)-3-oxopropanoic acid and N,N′-di(naphthyl-1-yl)malonamide were synthesised by the reaction of 1-naphthylamine with diethyl malonate under reflux. These two compounds were then separately cyclised to 4-hydroxybenzo[h]quinolin-2-(1H)-one in two different reactions in polyphosphoric acid. A series of esters and ethers of the 4-hydroxy group and some 3-substituted derivatives were prepared. The structures of the compounds were confirmed by infra-red NMR spectroscopy and elemental analysis.
References
1.
Refouvet B.
,
Guyon C.
,
Jacquot Y.
,
Girard C.
,
Fein H.
,
Bevalot F.
,
Robert J. F.
,
Heyd B.
,
Mantion G.
,
Richert L.
, and
Xicluna A.
, Eur. J. Med. Chem. , 2004 , 39 , 931 .
2.
Snider B.B.
, and
Wu X.
, Heterocycles , 2006 , 70 , 279 .
3.
Priya N.
,
Gupta A.
,
Chand K.
,
Singh P.
,
Kathuria A.
,
Raj H.
, and
Parmar V. S.
, Bioorg. Med. Chem. , 2010 , 18 , 4085 .
4.
Dube D.
,
Blouin M.
,
Brideau C.
,
Chan C. C.
,
Desmarais S.
,
Ethier D.
,
Falgueyret J. P.
,
Friesen R. W.
,
Girard M.
,
Girard Y.
,
Guay J.
,
Riendeau D.
,
Tagari P.
, and
Young R. N.
, Bioorg. Med. Chem. Lett. , 1998 , 8 , 1255 .
5.
Kidwai M.
,
Bhushan K. R.
,
Sapra P.
,
Saxena R. K.
, and
Gupta R.
, Bioorg. Med. Chem. , 2000 , 8 , 69 .
6.
Ziegler E.
, and
Junek H.
, Monatsch. Chem. , 1956 , 87 , 503 .
7.
Ziegler E.
,
Wolf R.
, and
Kappe Th.
, Monatsch. Chem. , 1964 , 96 , 418 .
8.
Kappe Th.
, and
Ziegler E.
, Monatsch Chem. , 1968 , 99 , 1943 .
9.
Kappe Th.
,
Sterk H.
, and
Ziegler E.
, Monatsch. Chem. , 1968 , 99 , 1950 .
10.
Ahvale A.B.
,
Prokopcová H.
,
Sefcovicová J.
,
Steinschifter W.
,
Täubl A. E.
,
Uray G.
, and
Stadlbauer W.
, Eur. J. Org. Chem. , 2008 , 563 .
11.
Kappe Th.
, II Farmaco , 1999 , 54 , 309 .
12.
Bowman E.
,
Campbell A.
, and
Tanner E. M.
, J. Chem. Soc. , 1959 , 444 .
13.
Kappe Th.
,
Karem A. S.
, and
Stadlbauer W.
, J. Heterocycl. Chem. , 1988 , 25 , 857 .
14.
Nadaraj V.
,
Selvi S. Th.
, and
Sasi R.
, ARKIVOC , 2006 , x , 82 .
15.
Park Su-J.
,
Lee J. C.
, and
Lee K. I. A.
, Bull. Korean Chem. Soc. , 2007 , 28 , 1203 .
16.
Sener I.
,
Karci F.
,
Ertan N.
, and
Kilic E.
, Dyes Pigm. , 2006 , 70 , 143 .
17.
Moradi Rufchahi E.O.
, Chin. Chem. Lett. , 2010 , 21 , 542 .
18.
Moradi Rufchahi E.O.
, and
Ghanadzadeh A.
, J. Mol. Liq. , 2011 , 160 , 160 .
19.
Moradi Rufchahi E.O.
, and
Ghanadzadeh Gilani A.
, Dyes Pigm. , 2012 , 96 , 632 .
20.
Moradi Rufchahi E.O.
,
Pouramir H.
,
Yazdanbakhsh M. R.
,
Yousefi H.
,
Bagheri M.
, and
Rassa M.
, Chin. Chem. Lett. , 2013 , 24 , 425 .
21.
Moradi Rufchahi E.O.
, and
Mohammadinia M.
, J. Mol. Liq. , 2014 , 199 , 393 .
22.
Lestina G.J.
, and
Regan T. H.
, J. Org. Chem. , 1969 , 34 , 1685 .
23.
Snavely F.A.
, and
Yoder C. H.
, J. Org. Chem. , 1968 , 33 , 513 .
24.
Yoder C.H.
,
Barth R. C.
,
Richter W. M.
, and
Snavely F. A.
, J. Org. Chem. , 1972 , 37 , 4121 .
25.
Shawali A.S.
,
Harb N. M. S.
, and
Badahdah K. O.
, J. Heterocycl. Chem. , 1985 , 22 , 1397 .
