Abstract
The reaction of 6,7-dihydroindolizin-8(5H)-one and an aromatic aldehyde yielded (E)-7-(arylmethylene)-6,7-dihydroindolizin-8(5H)-ones which underwent addition of bromoform in the presence of magnesium under N2 to give a novel series of 3-aryl-2,2-dibromo-5′H-spiro[cyclopropane-1,7′-indolizin]-8′(6′H)-one derivatives. The structures of the products were established by 1H NMR, 13C NMR, IR spectroscopy and mass spectra.
References
1.
Zhou H.Q.
,
Danger D.P.
,
Dock S.T.
,
Hawley L.
,
Roller S.G.
,
Smith C.D.
, and
Handlon A.L.
, Med. Chem. Lett. , 2010 , 1 , 19 .
2.
Li H.
,
Xia Z.Q.
,
Chen S.J.
,
Koya K.
,
Ono M.
, and
Sun L.J.
, Org. Process. Res. Dev. , 2007 , 11 , 246 .
3.
Kaloko J.
, and
Hayford A.
, Org. Lett. , 2005 , 7 , 4305 .
4.
Toyooka N.
,
Zhou D.
, and
Nemoto H.
, J. Org. Chem. , 2008 , 73 , 4575 .
5.
Amos R.I.J.
,
Gourlay B.S.
,
Molesworth P.P.
,
Smith J.A.
, and
Sprod O.R.
, Tetrahedron , 2005 , 61 , 8226 .
6.
Michael J.P.
, Nat. Prod. Rep. , 2007 , 24 , 191 .
7.
Dinsmore A.
,
Mandy K.
, and
Michael J.P.
, Org. Biomol. Chem. , 2006 , 4 , 1032 .
8.
Baudoin O.
,
Cesario M.
,
Guénard D.
, and
Guéritte F.
, J. Org. Chem. , 2002 , 67 , 1199 .
9.
Jirkovsky I.
,
Santroch G.
,
Baudy R.
, and
Oshirot G.
, J. Med. Chem. , 1987 , 30 , 388 .
10.
Gomi S.
,
Ikeda D.
,
Nakamura H.
,
Naganawa H.
,
Yamashita F.
,
Hotta K.
,
Kondo S.
,
Okami Y.
,
Umezawa H.
, and
Iitaka Y.
, J. Antibiot. , 1984 , 37 , 1491 .
11.
Niwa H.
,
Wakamatsu K.
, and
Yamada K.
, Tetrahedron Lett. , 1989 , 30 , 4543 .
12.
Hanson J.R.
,
Marten T.
, and
Nyfeler R.J.
, J. Chem. Soc., Perkin Trans I. , 1976 , 876 .
13.
Braunholtz J.T.
,
Mallion K.B.
, and
Mann F.G.
, J. Chem. Soc. , 1962 , 4346 .