Abstract
The 1:1 intermediate generated by the addition of alkyl and aryl isocyanides to dialkyl acetylenedicarboxylate is trapped by 1,2-dicarbonyl compounds such as 1,10-phenanthroline-5,6-dione (phendione) to yield iminolactones in good yields.
References
1.
Beck B.
,
Magnin-Lachaux M.
,
Herdtweck E.
, and
Domling A.
, Organic Lett. , 2001 , 3 , 2875 .
2.
Oliaruso M.A.
, and
Wolfe J. F.
, In Synthesis of Lactones and Lactams , John Wiley & Sons , New York , 1993 .
3.
Dider V.
, and
Liang L.
, Synthetic Communications. , 2003 , 33 , 1575 .
4.
For reviews on furan-2(5H)-ones (but-2-en-4-olides) See: (a)
Rao Y.S.
, Chem. Rev. , 1964 , 64 , 353 .
5.
Rao Y.S.
, Chem. Rev. , 1976 , 76 , 625 .
6.
Avetisyan A.A.
, and
Dangyan M. T.
, Russ. Chem. Rev. , 1977 , 46 , 643 .
7.
(a)
Rupprecht J.K.
,
Hui Y. H.
, and
Mclaughlin J. L.
, J. Nat. Prod. , 1990 , 53 , 237 .
8.
Zeng L.
,
Ye Q.
,
Oberlis G.
,
Shi N. H.
,
Gu Z. M.
,
He K.
, and
Mclaughlin J. L.
, J. Nat. Prod. Rep. , 1996 , 13 , 275 .
9.
Cavallito C.
, J. Med. Chem. , 1951 , 1 , 221 .
10.
Restock T.L.
, and
Sell H. M.
, J. Am. Chem. Soc. , 1952 , 74 , 274 .
11.
Payne G.B.
, U.S. Patent 3177227, 1965 , Chem. Abstr. , 1965, 63 , 6866e.
12.
Winterfeldt E.
,
Schumann D.
, and
Dillinger H. J.
, Chem. Ber. , 1969 , 102 , 1656 .
13.
Oakes T.R.
,
David H. G.
, and
Nagel F.
, J. Am. Chem. Soc. , 1969 , 91 , 4761 .
14.
Takisawa T.
,
Obata N.
,
Suzuki Y.
, and
Yanagida T.
, Tetrahedron Lett. , 1969 , 3407 .
15.
Ugi I.
, Isonitrile Chemistry , Academic press , london , 1971 .
16.
Ugi I.
, Angew. Chem., Int. Ed. Engl. , 1982 , 21 , 810 .
17.
Yavari I.
, and
Maghsoodlou M. T.
, J. Chem. Res. , 1998 , 386 .
18.
Nair V.
,
Rajesh C.
,
Vinod A. U.
,
Bindu S.
,
Sreekanth A. R.
,
Mathen J. S.
, and
Balagopal L.
, Acc. Chem. Res. , 2003 , 36 , 899 .
19.
Nair V.
,
Vinod A. U.
, and
Rajesh C.
, J. Org. Chem. , 2001 , 66 , 4427 .
20.
Oakes T.R
, and
Donovan D. J.
, J. Org. Chem. , 1973 , 38 , 1319 .
21.
Dillinger H.J.
,
Fengler G.
,
Schumann D.
, and
Winterfeldt E.
, Tetrahedron. , 1974 , 30 , 2553 .
22.
Dillinger H.J.
,
Fengler G.
,
Schumann D.
, and
Winterfeldt E.
, Tetrahedron. , 1974 , 30 , 2561 .
23.
Johanson F.A.
,
Gulbenkian A. H.
, and
Nasutavicus W. A.
, Chem. Commun. , 1970 , 608 .
24.
yavari I.
,
Adib M.
, and
Sayahi M. H.
, Tetrahedron Lett. , 2002 , 43 , 2927 .
25.
Grieco P.A.
, Synthesis. , 1985 , 67 .
26.
Yamagida M.
,
Tanaka Y.
, and
Yoshimoto Y.
, Bull. Chem. Soc. Jpn. , 1992 , 65 , 10061 .
27.
Bodig S.
, and
MacDonnell F. M.
, Tetrahedron Lett. , 1997 , 38 , 8159 .