Abstract
Protonation of the reactive intermediates produced in the reaction between alkyl isocyanides and dialkyl acetylenedicarboxylates by carboxylic acids leads to vinylnitrilium cations which then undergo nucleophilic addition of the conjugate bases of the carboxylic acids. This intermediate rearranges to produce dialkyl (E)2-{[(aryl)acetyl(alkyl-amino)]carbonyl}-2-butenedioate derivatives.
References
1.
Ugi I.
,
Werner B.
, and
Domling A.
, Molecules , 2003 , 8 , 53 .
2.
Domling A.
, Curr. Opin. Chem. Biol. , 2000 , 4 , 318 .
3.
Domling A.
, Chem. Rev. , 2006 , 106 , 17 .
4.
Passerini M.
, Gazz. Chim. Ital. , 1921 , 51 II , 126 .
5.
Nair V.
,
Menon R.S.
, and
Sreekumar V.
, Pure Appl. Chem. , 2005 , 77 , 1191 .
6.
Nair V.
,
Menon R.S.
,
Deepthi A.
,
Devi B.R.
, and
Biju A.T.
, Tetrahedron Lett. , 2005 , 46 , 1337 .
7.
Nair V.
, and
Deepthi A.
, Tetrahedron Lett. 2006 , 47 , 2037 .
8.
Alizadeh A.
,
Rostamnia S.
,
Zohreh N.
, and
Bijanzadeh H.R.
, Month. Chem. , 2008 , 139 , 49 .
9.
Anary-Abbasinejad M.
,
Mosslemin M.H.
,
Anaraki-Ardakani H.
, and
Tahan S.
, J. Chem. Res. , 2006 , 30 , 306 .
10.
Anary-Abbasinejad M.
,
Mosslemin M.H.
,
Tahan S.
, and
Anaraki-Ardakani H.
, J. Chem. Res. , 2006 , 30 , 170 .
11.
Anary-Abbasinejad M.
,
Anaraky-Ardakani H.
,
Rastegari F.
, and
Hassanabadi A.
, J. Chem. Res. , 2007 , 31 , 602 .
12.
Yavari I.
,
Djahaniani H.
, and
Nasiri F.
, Tetrahedron , 2003 , 59 , 9409 .
13.
Shaabani A.
,
Teimouri M.B.
, and
Bijanzadeh H.R.
, J. Chem. Res. , 2002 , 26 , 381 .
14.
Shaabani A.
,
Teimouri M.B.
,
Mirzaei P.
, and
Bijanzadeh H.R.
, J. Chem. Res. , 27 , 2003 , 82 .
15.
Alizadeh A.
,
Rostamnia S.
, and
Hu M.L.
, Synlett , 2006 , 1592 .
16.
Mosslemin M.H.
,
Nateghi M.R.
,
Hassanabadi A.
, and
Zare M.
, J. Chem. Res. , 2010 , 34 , 178 .
17.
Anary-Abbasinejad M.
,
Hassanabadi A.
, and
Aiinparast F.
, J. Chem. Res. , 2010 , 34 , 613 .
18.
Eliel E.L.
,
Wilen S.H.
, and
Mander L.N.
, Stereochemistry of organic compounds , Wiley , New York , 1994 , p. 569 .
19.
Ugi I.
, Isonitrile chemistry , Academic , London , 1971 .
20.
Ugi I.
, Angew. Chem., Int. Ed. Engl. , 1982 , 21 , 810 .
21.
Dömling A.
, and
Ugi I.
, Angew. Chem., Int. Ed. 2000 , 39 , 3168 .
22.
Nair V.
,
Viond A.U.
,
Nair J.S.
,
Sreekanth A.R.
,
Rath N.P.
, Tetrahedron Lett. , 2000 , 41 , 6675 .
23.
Walborsky H.M.
, and
Presiasamy M.P.
, The chemistry of functional groups, supplement C ,
Patai S.
, and
Rappaport Z.
, eds, Wiley , New York , 1983 ; Chap. 20, p 835 .
24.
Marcaccini S.
, and
Torroba T.
, Org. Prep. Proc. Int. , 1993 , 25 , 141 .
25.
Baker R.H.
, and
Stanonis D.
, J. Am. Chem. Soc. , 1951 , 73 , 699 .
26.
Ugi I.
, Pure Appl. Chem. , 2001 , 77 , 187 .
27.
Bock H.
, and
Ugi I.
, J. Prakt. Chem. , 1997 , 339 , 385 .
