Abstract
The rhodium (II) acetate-catalysed decomposition of 3-diazobenzopyran-2,4(3H )-dione in the presence of a terminal alkyne gave rise to a mixture of isomeric 2-substituted
furo[3,2-c ]coumarin and furo[2,3-b ]coumarin, resulting from a formal [3+2] cycloaddition.
Key words
heterocyclisation - furocoumarins - diazocoumarins - diazocarbonyl compounds - rhodium
carbene
References
<A NAME="RP07300SS-1">1 </A>
Silberad O.
Roy JC.
J. Chem. Soc.
1906,
89:
179
<A NAME="RP07300SS-2">2 </A>
Taber DF.
Ruckle RE.
J. Am. Chem. Soc.
1986,
108:
7686
<A NAME="RP07300SS-3">3 </A>
Taber DF.
Raman K.
J. Am. Chem. Soc.
1983,
105:
5935
<A NAME="RP07300SS-4">4 </A>
Heslin JC.
Moody CJ.
Slawin AMZ.
Williams DJ.
Tetrahedron Lett.
1986,
27:
1403
<A NAME="RP07300SS-5">5 </A>
Paulissen R.
Reimlinger H.
Hayez E.
Hubert AJ.
Teyssié P.
Tetrahedron Lett.
1973,
2233
<A NAME="RP07300SS-6">6 </A>
Doyle MP.
McKervey MA.
Ye T.
Modern Catalytic Methods for Organic Synthesis with Diazo Compounds
Wiley;
New York:
1997.
<A NAME="RP07300SS-7">7 </A>
Taber DF.
Comprehensive Organic Synthesis
Vol. 3; Pattenden, G. Ed.; Pergamon;
Oxford:
1991.
<A NAME="RP07300SS-8">8 </A>
Doyle MP.
Homogeneous Transition-Metal Catalysis in Organic Chemistry
Moser W. R., Slocum D. W. Eds.; ACS Advanced Chemistry Series, No. 230, American Chemical
Society;
Washington:
1992.
ch. 30.
<A NAME="RP07300SS-9">9 </A>
Padwa A.
Austin DJ.
Angew. Chem., Int. Ed. Engl.
1994,
33:
1797
<A NAME="RP07300SS-10">10 </A>
Ye T.
McKervey MA.
Chem. Rev.
1994,
94:
1091
<A NAME="RP07300SS-11">11 </A>
Doyle MP.
Chem.Rev.
1986,
86:
547
<A NAME="RP07300SS-12">12 </A>
Doyle MP.
Comprehensive Organometallic Chemistry (Transition-Metal Carbene Complexes: Diazo-Decomposition,
Ylide and Insertion)
Vol. 12; Abel E. W., Stone F. G. A., Wilkinson G. Eds.; Pergamon;
Oxford:
1995.
<A NAME="RP07300SS-13">13 </A>
Doyle MP.
Forbes DC.
Chem. Rev.
1998,
98:
911
<A NAME="RP07300SS-14">14 </A>
Cenini S.
Cravotto G.
Giovenzana GB.
Palmisano G.
Tollari S.
Tetrahedron
1999,
55:
6577
<A NAME="RP07300SS-15">15 </A>
Cenini S., Cravotto G., Giovenzana G. B., Palmisano G., Penoni A., Tollari S., unpublished
results.
<A NAME="RP07300SS-16">16 </A>
Huebneck CF.
Ink KP.
J. Am. Chem. Soc.
1945,
67:
97
<A NAME="RP07300SS-17">17 </A>
Lee YR.
Suk JY.
Kim BS.
Tetrahedron Lett.
1999,
40:
6603
<A NAME="RP07300SS-18">18 </A>
Misky M.
Jakupovic J.
Phytochemistry
1990,
29:
1995
<A NAME="RP07300SS-19">19 </A>
Schuster N.
Christiansen C.
Jakupovic J.
Mungai M.
Phytochemistry
1993,
34:
1179
<A NAME="RP07300SS-20">20 </A>
Bittner M.
Jakupovic J.
Grenz M.
Silva M.
Phytochemistry
1988,
27:
3263
<A NAME="RP07300SS-21">21 </A>
Rustalyan A.
Nazarians L.
Bohlmann F.
Phytochemistry
1980,
19:
1254
<A NAME="RP07300SS-22">22 </A>
Zdero C.
Bolhmann F.
King RM.
Robinson H.
Mungai M.
Phytochemistry
1986,
25:
509
<A NAME="RP07300SS-23">23 </A>
Bohlmann F.
Zdero C.
Phytochemistry
1977,
16:
1261
<A NAME="RP07300SS-24">24 </A>
We are investigating the synthetic potential of this reaction (e. g., insertion into
aromatic systems) and will report our findings in due course (Cenini S., Giovenzana
G.B., Goldoni L., Palmisano G., Penoni A., Tollari, S., unpublished results).
<A NAME="RP07300SS-25">25 </A>
Rosenfeld MJ.
Ravi Shankar BK.
Shechter H.
J. Org. Chem.
1988,
53:
2699
<A NAME="RP07300SS-26">26 </A>
Monahan AS.
Freilich JD.
Fong JL.
Tetrahedron Lett.
1970,
1865
<A NAME="RP07300SS-27">27 </A>
Walker JA.
Orchin M.
J. Chem. Soc., Chem. Commun.
1968,
1239
<A NAME="RP07300SS-28">28 </A>
Fiato RA.
Mushak P.
Battiste MA.
J. Chem. Soc.,Chem. Commun.
1975,
869
<A NAME="RP07300SS-29">29 </A> The ring opening of metallacyclobutenes is well precedented, see:
Tebbe FN.
Harlow RL.
J. Am. Chem. Soc.
1980,
102:
6151
<A NAME="RP07300SS-30">30 </A>
York EJ.
Dittmar W.
Stevenson RJ.
Bergman R.
J. Am. Chem. Soc.
1973,
95:
5680
<A NAME="RP07300SS-31">31 </A>
York EJ.
Dittmar W.
Stevenson RJ.
Bergman R.
J. Am. Chem. Soc.
1972,
94:
2882
<A NAME="RP07300SS-32">32 </A>
Al-Dulayami J.
Baird MS.
Clegg W.
Tetrahedron Lett.
1988,
6149
<A NAME="RP07300SS-33">33 </A>
Padwa A.
Fryxell JE.
Advances in Strain in Organic Chemistry
Vol.1; Halton B. Ed.; JAI;
Greenwich:
1991.
<A NAME="RP07300SS-34">34 </A>
Pincock JA.
Moutsakapas AA.
Can. J. Chem.
1977,
55:
979
<A NAME="RP07300SS-35">35 </A>
Padwa A.
Acc. Chem. Res.
1979,
12:
310
<A NAME="RP07300SS-36">36 </A>
Hoye TR.
Dinsmore CJ.
Johnson DSKorkowski PF.
J. Org. Chem.
1990,
55:
4518
<A NAME="RP07300SS-37">37 </A>
Padwa A.
Hornbuckle SH.
Chem. Rev.
1991,
91:
263
<A NAME="RP07300SS-38">38 </A>
Appendino G.
Cravotto G.
Giovenzana GB.
Palmisano G.
J. Nat. Prod.
1999,
62:
1627
<A NAME="RP07300SS-39">39 </A>
Appendino G.
Cravotto G.
Palmisano G.
Annunziata R.
Synth.Commun.
1996,
26:
33
<A NAME="RP07300SS-40">40 </A>
Appendino G.
Cravotto G.
Palmisano G.
Annunziata R.
Tetrahedron
1998,
54:
10819
<A NAME="RP07300SS-41">41 </A>
Darbarwar M.
Sundaramurthy W.
Synthesis
1982,
337
<A NAME="RP07300SS-42">42 </A>
Lee YR.
Kim BS.
Tetrahedron Lett.
1997,
38:
2095
<A NAME="RP07300SS-43">43 </A>
Lee YR.
Suk JY.
Kim BS.
Org. Lett.
2000,
2:
1387
<A NAME="RP07300SS-44">44 </A>
Kobayashi H.
Sakashita K.
Akamatsu H.
Tanaka K.
Uchida M.
Uneda T.
Kitamura T.
Morikawa O.
Konishi H.
Heterocycles
1999,
51:
2881
<A NAME="RP07300SS-45">45 </A>
Taber DF.
You K.
Song Y.
J. Org. Chem.
1995,
60:
1093