Abstract
An efficient pseudo four-component reaction between substituted 2-hydroxybenzaldehydes, ammonium acetate and different dialkyl but-2-ynedioates for the preparation of (2E)-2-(6H,12H-6,12-epiminodibenzo[b,f][1,5]dioxocin-13-yl)but-2-enedioates in moderate to good yields (60–83%) was developed. This method uses a variety of cheap and readily available reactants and a wide range of substrates. The structure of a typical product was confirmed by X-ray crystallography.
Keywords
References
1.
Asghari S.
,
Malekian N.
,
Esmaeilpour R.
,
Ahmadipour M.
, and
Mohseni M.
, Chin. Chem. Lett. , 2014 , 25 , 1441 .
2.
Gammill R.B.
,
Bisaha S.N.
,
Timko J.M.
,
Judge T.M.
,
Barbachyn M.R.
, and
Kim K.S.
, WO Patent: 9006307, issued 26 July 1990 .
3.
Xie W.
,
Peng H.
,
Zalkow L.H.
,
Li Y.-H.
,
Zhu C.
,
Powis G.
, and
Kunkel M.
, Bioorg. Med. Chem. , 2000 , 8 , 699 .
4.
Huber I.
,
Zupko I.
,
Kovacs I.J.
,
Minorics R.
,
Gulyas-Fekete G.
,
Maasz G.
, and
Perjesi P.
, Monatsh. Chem. , 2015 , 146 , 973 .
5.
Bodenteich A.
,
Frantsits W.J.
,
Pirich E.
, and
Czollner L.
, WO Patent: 2005030332, issued 7 April 2005 .
6.
Hua Z.-Q.
,
Li M.
,
Liu M.-D.
,
Zhuang W.-M.
, and
Li G.-K.
, Dyes Pigments , 2013 , 96 , 71 .
7.
Harmata M.
,
Barnes C.L.
,
Karra S.R.
, and
Elahmad S.
J. Am. Chem. Soc. , 1994 , 116 , 8392 .
8.
Paliwal S.
,
Geib S.
, and
Wilcox C.S.
J. Am. Chem. Soc. , 1994 , 116 , 4497 .
9.
Black D. St. C.
,
Craig D.C.
,
Kumar N.
, and
McConnell D.B.
, Tetrahedron Lett. , 1996 , 37 , 241 .
10.
Mitra K.
, and
Gates K.S.
, Tetrahedron Lett. , 1995 , 36 , 1391 .
11.
Bag B.G.
, and
Maitra U.
, Synth. Commun. , 1995 , 25 , 1849 .
12.
Rebek J.
Jr.
, Acc. Chem. Res. , 1990 , 23 , 399 .
13.
Mandal D.
,
Wu A.-Q.
,
Guo G.-C.
, and
Ray D.
, Inorg. Chem. , 2006 , 45 , 8826 .
14.
Black D.
,
Craig D.C.
,
Kumar N.
, and
McConnell D.B.
, Tetrahedron Lett. , 1996 , 37 , 241 .
15.
Wilcox C.S.
,
Adrian J.C.
,
Webb T.H.
, and
Zawacki F.J.
, J. Am. Chem. Soc. , 1992 , 114 , 10189 .
16.
Salez H.
,
Wardani A.
,
Demeunynck M.
,
Tatibouet A.
, and
Lhomme J.
Tetrahedron Lett. , 1995 , 36 , 1271 .
17.
Wilen S.H.
,
Qi J.Z.
, and
Williard P.G.
J. Org. Chem. , 1991 , 56 , 485 .
18.
Bachet P.B.
, and
Guidi-Morosini C.B.
, Acta Crystallogr. C , 1986 , C42 , 1630 .
19.
Refat H.M.
,
Fadda A.A.
,
Lu Y.
, and
Blehl E.R.
, Heterocycles , 1996 , 43 , 977 .
20.
Jones P.R.
, and
Gelinas R.M.
, J. Org. Chem. , 1981 , 46 , 195 .
21.
Panja S.K.
,
Dwivedi N.
, and
Saha S.
, RSC Adv. , 2016 , 6 , 59574 .
22.
Jeffrey G.A.
, and
Saenger W.
, Hydrogen bonding in biological structures. Springer-Verlag , New York , 1991 .
23.
Arunan E.
,
Desiraju G.R.
,
Klein R.A.
,
Sadlej J.
,
Scheiner S.
,
Alkorta I.
,
Clary D.C.
,
Crabtree R.H.
,
Dannenberg J.J.
,
Hobza P.
,
Kjaergaard H.G.
,
Legon A.C.
,
Mennucci B.
, and
Nesbitt D. J.
, Pure Appl. Chem. , 2011 , 83 , 1619 .
24.
Novikov P.V.
,
Malyshev O.R.
,
Lyssenkoc K.A.
, and
Kostyanovsky R.G.
, Mendeleev Commun. , 2004 , 14 , 310 .
25.
Kostyanovsky R.G.
,
Elnatanov Y.I.
,
Chervin I.I.
,
Konovalikhin S.V.
,
Zolotoi A.B.
, and
Atovmyan L.O.
, Mendeleev Commun. , 1996 , 6 , 143 .
26.
Voskressensky L.G.
,
Borisova T.N.
,
Titov A.A.
,
Listratova A.V.
,
Kulikova L.N.
,
Varlamov A.V.
,
Khrustalev V.N.
, and
Aleksandrovc G.G.
, Russ. Chem. Bull. Int. Ed. , 2012 , 61 , 1231 .
27.
Varlamov A.V.
,
Borisova T.N.
,
Voskresenskii L.G.
, and
Titov A.A.
, RU Patent: 2397984, issued 28 July 2010 .