Abstract
The reactions of a series of alkyl X-phenylpropiolates with 2-hydroxy-1-naphthaldehyde and triphenylphosphine led to benzochromenes in moderate yields. When the reactions were performed in the presence of bis(4-methoxyphenyl)phenylphosphine instead of triphenylphosphine, the rate and yields of the reactions increased. Reaction yields were enhanced for alkyl X-phenylpropiolates when X was an electron-deficient substituent such as CF3 or Cl, thus showing that the electronic effect of substituents plays an important role in the reactions.
Keywords
References
1.
Lukashenko A.V.
,
Osyanin V.A.
,
Osipov D.V.
, and
Klimochkin Y.N.
, J. Org. Chem. , 2017 , 82 , 1517 .
2.
Mohr S.J.
,
Chirigos M.A.
,
Fuhrman F.S.
, and
Pryor J.W.
, Cancer Res. , 1975 , 35 , 3750 .
3.
Sangani C.B.
,
Shah N.M.
,
Patel M.P.
, and
Patel R.G.
, J. Serb. Chem. Soc. , 2012 , 77 , 1165 .
4.
Tandon V.K.
,
Vaish M.
,
Jain S.
,
Bhakuni D.S.
, and
Srimal R.C.
, Indian J. Pharm. Sci. , 1991 , 53 , 22 .
5.
Cheng J.F.
,
Ishikawa A.
,
Ono Y.
,
Arrhenius T.
, and
Nadzan A.
, Bioorg. Med. Chem. Lett. , 2003 , 13 , 3647 .
6.
Thareja S.
,
Verma A.
,
Kalra A.
,
Gosain S.
,
Rewatkar P.V.
, and
Kokil G.R.
, Acta Pol. Pharm. , 2010 , 67 , 423 .
7.
Aliaa M.K.
,
Manal M.K.
,
Eman K.A.
, and
Heba A.H.
, Int. J. Pharmaceut. Res. Dev. , 2012 , 4 , 310 .
8.
Karia D.C.
,
Pandya H.K.
,
Godvani N.K.
, and
Shah A.
, Elixir Org. Chem. , 2012 , 47 , 8797 .
9.
Johnson A.W.
, Ylides and imines of phosphorus. Wiley , New York , 1993 , chap. 1, p. 1 .
10.
Neochoritis C.G.
,
Zarganes-Tzitzikas T.
, and
Stephanidou-Stephanatou J.
, Synthesis , 2014 , 46 , 537 .
11.
Yavari I.
, and
Ramazani A.
, Synth. Commun. , 1997 , 27 , 1385 .
12.
El-Shaieb K.M.
,
Shaker R.M.
, and
Aly A.A.
, Synth. Commun. , 2008 , 38 , 2054 .
13.
Asghari S.
,
Firouzzade Pasha G.
, and
Tajbakhsh M.
, Phosphorus Sulfur Silicon Relat. Elem. , 2016 , 191 , 939 .
14.
Asghari S.
,
Sobhaninia Z.
, and
Naderi Z.
, Acta Chim. Slov. , 2008 , 55 , 434 .
15.
Asghari S.
,
Salimi A.
, and
Taghipour V.
, Phosphorus Sulfur Silicon Relat. Elem. , 2012 , 187 , 669 .
16.
Dückert H.
,
Khedkar V.
,
Waldmann H.
, and
Kumar K.
, Chem. Eur. J. , 2011 , 17 , 5130 .
17.
Eschenbrenner-Lux V.
,
Dückert H.
,
Khedkar V.
,
Bruss H.
,
Waldmann H.
, and
Kumar K.
, Chem. Eur. J. , 2013 , 19 , 2294 .
18.
Nishimura Y.
,
Kawamura Y.
,
Watanabe Y.
, and
Hayashi M.
, J. Org. Chem. , 2010 , 75 , 3875 .
19.
Deng J.C.
,
Chan F.W.
,
Kuo C.W.
,
Cheng C.A.
,
Huang C.Y.
, and
Chuang S.C.
, Eur. J. Org. Chem. , 2012 , 29 , 5738 .
20.
Corey E.J.
, and
Fuchs P.L.
, Tetrahedron Lett. , 1972 , 13 , 3769 .
21.
Sahu B.
,
Muruganantham R.
, and
Namboothiri I.N.
, Eur. J. Org. Chem. , 2007 , 15 , 2477 .
22.
Morris J.
, and
Wishka D.G.
, Synthesis , 1994 , 1 , 43 .
23.
Blanco V.D.
, and
Doronzo S.
, Inorganic syntheses , ed.
Douglas B.E.
. Wiley , New York , 1978 , Vol. XVIII , pp. 169 –173 .