Abstract
The reaction of dialkyl acetylenedicarboxylates with the N–H acid 4-phenyl-[1,2,4]triazolidine-3,5-dione in the presence of trialkyl(aryl) phosphites at reflux temperature led to the title phosphonato ester derivatives. The configurations of the compounds were determined (2R*, 3S* and mirror image) using the coupling constants and the Karplus equation.
Keywords
References
1.
Yavari I.
,
Islami M.R.
, and
Bijanzadeh H.R.
, Tetrahedron , 1999 , 55 , 5547 .
2.
Yavari I.
, and
Ramazani A.
, Phosphorus, Sulphur, Silicon , 1997 , 130 , 73 .
3.
Maghsoodlou M.T.
,
Habibi-Khorassani S.M.
,
Rofouei M.K.
,
Adhamdoust S.R.
, and
Nassiri M.
, Arkivoc , 2006 , (xii ),138.
4.
Corbridge D.E.C.
, Phosphorus, an outline of chemistry, biochemistry and uses , 5th edn, Elsevier , Amsterdam , 1995 .
5.
Castelot-Deliencourt G.
,
Pannecoucke X.
, and
Quirion J-C.
, Tetrahedron Lett. , 2001 , 42 , 1025 .
6.
Cohen R.J.
,
Fox D.L.
,
Eubank J.F.
, and
Salvatore R.N.
, Tetrahedron Lett. , 2003 , 44 , 8617 .
7.
Amiguse E.J.
, and
Migaud M.E.
, Tetrahedron Lett. , 2004 , 45 , 1001 .
8.
Rassukana Y.V.
,
Onysko P.P.
,
Davydova K.O.
, and
Sinitsa A.D.
, Tetrahedron Lett. , 2004 , 45 , 3899 .
9.
Lefebver I.M.
, and
Evans S.A.
Jr.
, J. Org. Chem. , 1997 , 62 , 7532 .
10.
Kim S.K.
,
Hurh E.Y.
,
Youn J.N.
, and
Park J.I.
, J. Org. Chem. , 1999 , 64 , 9272 .
11.
Joly D.G.
, and
Jacobsen E.N.
, J. Am. Chem. Soc. , 2004 , 126 , 4102 .
12.
Quin D.L.
, A guide to organophosphorus chemistry , John Wiley & Sons , New York , 2000 .
13.
Walker B.J.
, Organophosphorus chemistry , Penguin Education , New York , 1972 .
14.
Goodman A.
, and
Gilman
,
Hardman J.G.
, and
Limbird L.E.
, The pharmacological basis of therapeutics , 10 edn, McGraw-Hill , New York , 2001 .
15.
Gallant J.E.
, and
Pham P.A.
, Expert Rev. Anti-infect. Ther. , 2003 , 1 , 415 .
16.
Hassanabadi A.
,
Mosslemin M.H.
,
Anary-Abbasinejad M.
, and
Khalesi H.
, Synth. Commun. , 2011 , 41 , 1529 .
17.
Anary-Abbasinejad M.
,
Rostami N.
,
Parhami A.
, and
Hassanabadi A.
, J. Chem. Res. , 2007 , 257 .
18.
Anary-Abbasinejad M.
,
Hassanabadi A.
, and
Anaraki-Ardakani H.
, J. Chem. Res. , 2007 , 455 .
19.
Anary-Abbasinejad M.
,
Charkhati K.
, and
Hassanabadi A.
, J. Chem. Res. , 2009 , 33 , 319 .
20.
Hassanabadi A.
,
Anary-Abbasinejad M.
,
Dehghan A.
,
Taraghi F.
, and
Shams N.
, J. Chem. Res. , 2011 , 35 , 368 .
21.
Karplus M.
, J. Am. Chem. Soc. , 1963 , 85 , 2870 .
22.
Haasnot C.A.G.
,
De Leeuw F.A.A.M.
, and
Altona C.
, Tetrahedron , 1980 , 36 , 2783 .
23.
Breitmaier E.
, and
Voelter W.
, Carbon-13 NMR spectroscopy , 3rd edn, VCH , New York , 1990 , 250 .
