Abstract
Tosyl isocyanide and ethyl chloroformate react with nitrostyrenes
to afford nitro-substituted pyrroles in good yield when a catch-and-release
protocol was employed as a purification strategy.
Key words
pyrroles - immobilized reagents - heterocycles - multi-component
References
1a Davies DT.
Aromatic Heterocyclic
Chemistry
OUP;
Oxford:
1992.
1b Barton D.
Ollis WD.
Sammes PG.
Comprehensive Organic Chemistry
Vol.
4:
Jackson AH.
Pergamon
Press;
Oxford:
1979.
p.276
1c Lesage S.
Xu H.
Durham L.
Hydrol.
Sci. J.
1993,
38:
343
1d Dolphin D.
Academic Press;
New
York:
1977.
1e Joh Y.
Kotate Y.
Macromolecules
1970,
3:
337
1f Anez M.
Uribe G.
Mendoza L.
Contreras R.
Synthesis
1981,
214
2a Hui F.
Peng P.
Hamann MT.
Hu J.-F.
Chem.
Rev.
2008,
108:
264
2b Wang W.
Namikoshi M.
Heterocycles
2007,
74:
53
2c Morris JC.
Phillips AJ.
Nat.
Prod. Rep.
2008,
25:
95
2d Hughes CC.
Prieto-Davo A.
Jensen
PR.
Fenical W.
Org.
Lett.
2008,
10:
629
2e Donohoe
TJ.
Thomas RE.
Chem.
Rec.
2007,
7:
180
2f Walsh
CT.
Garneau-Tsodikova S.
Howard-Jones AR.
Nat. Prod. Rep.
2006,
23:
517
2g Gupton JT. In Topics in Heterocyclic
Chemistry
Springer;
Berlin/Heidelberg:
2006.
p.53-92
3a Nogami T.
Shigehara Y.
Matsuda N.
Takahashi Y.
Naganawa H.
Nakamura H.
Hamada M.
Muraoka Y.
Takita T.
Iitaka T.
Takeuchi T.
J. Antibiot.
1990,
43:
1192
3b Jacobi PA.
Coults LD.
Guo JS.
Leung
SI.
J.
Org. Chem.
2000,
65:
205
3c Fürstner A.
Angew. Chem. Int. Ed.
2003,
42:
3582
3d Domingo VM.
Aleman C.
Brillas E.
Julia L.
J. Org. Chem.
2001,
66:
4058
3e Hong F.
Zaidi J.
Pang Y.-P.
Cusack B.
Richelson E.
J.
Chem. Soc., Perkin Trans. 1
1997,
2997
3f Lea AP.
McTavish D.
Drugs
1997,
53:
828
3g Higasio YS.
Shoji T.
Appl. Catal.,
A
2001,
221:
197
3h Sigman DS.
Chen CB.
Annu.
Rev. Biochem.
1990,
59:
207
3i Skotheim TA.
Handbook of Conducting Polymers
Marcel
Dekker;
New York:
1986.
4a De Kimpe N.
Abbaspour TK.
Stevens C.
De Cooman P.
Tetrahedron
1997,
53:
3693 ; and references cited therein
4b Crawley ML.
Goljer I.
Jenkins DJ.
Mehlmann
JF.
Nogle L.
Dooley R.
Mahaney PE.
Org. Lett.
2006,
8:
5837
4c Martin R.
Rivero MR.
Buchwald SL.
Angew. Chem. Int. Ed.
2006,
45:
7079
4d Larionov OV.
de Meijere A.
Angew.
Chem. Int. Ed.
2005,
117:
5809
4e Gorin DJ.
Davis NR.
Toste FD.
J. Am. Chem. Soc.
2005,
127:
11260
4f Aydogan F.
Demir AS.
Tetrahedron
2005,
61:
3019
4g Chien T.-C.
Meade EA.
Hinkley JM.
Townsend LB.
Org.
Lett.
2004,
6:
2857
4h Ramanathan B.
Keith AJ.
Armstrong D.
Odom
AL.
Org. Lett.
2004,
6:
2957
4i Trofimov BA.
Zaitsev AB.
Schmidt EY.
Vasil’tsov AM.
Mikhaleva AI.
Ushakov IA.
Vashchenko AV.
Zorina NV.
Tetrahedron Lett.
2004,
45:
3789
4j Almerico AM.
Montalbano A.
Diana P.
Barraja P.
Lauria A.
Cirrincione G.
Dattolo G.
ARKIVOC
2001,
(vi):
129
4k Trofimov BA.
Markova MV.
Morozova LV.
Mikhaleva AI.
ARKIVOC
2001,
(ix):
24
4l Trofimov
BA.
Tarasova OA.
Mikhaleva AI.
Kalinina NA.
Sinegovskaya LM.
Henkelmann J.
Synthesis
2000,
1585
5a Van Leusen AM.
Siderius H.
Hoogenboom BE.
van Leusen D.
Tetrahedron
Lett.
1972,
52:
5337
5b ten Have R.
Leusink FR.
van
Leusen AM.
Synthesis
1996,
871
6a Barton DHR.
Zard SZ.
J. Chem. Soc., Chem. Commun.
1985,
1098
6b Barton DHR.
Kervagoret J.
Zard SZ.
Tetrahedron
1990,
21:
7587
6c Bergman J.
Rehn S.
Tetrahedron
2002,
58:
9179
7a Cohen BJ.
Kraus MA.
Patchornik A.
J. Am. Chem. Soc.
1977,
99:
4165
7b Cainelli G.
Contento M.
Manescalchi F.
Regnoli R.
J. Chem. Soc., Perkin Trans.
1
1980,
2516
7c Cohen BJ.
Kraus MA.
Patchornik A.
J. Am. Chem. Soc.
1981,
103:
7620
7d Bergbreiter DE.
Chem.-Tech.
1987,
17:
686
7e Brown SD.
Armstrong
RW.
J.
Am. Chem. Soc.
1996,
118:
331
7f Wentworth P.
Janda KD.
Chem. Commun.
1999,
1917
8a Solinas A.
Taddei M.
Synthesis
2007,
2409
8b Bhattacharyya S.
Mol.
Diversity
2005,
9:
253
8c Storer RI.
Takemoto T.
Jackson PS.
Brown DS.
Baxendale IR.
Ley SV.
Chem.-Eur. J.
2004,
10:
2529
8d Kirschning A.
Wittenberg R. In Merging
Solid-Phase and Solution-Phase Synthesis - The ”Resin-Capture-Release"
Hybrid Technique, Organic Synthesis Highlights V
Wiley-VCH;
Weinheim:
2003.
p.265-279
8e Ley SV.
Baxendale IR.
Chem. Rec.
2002,
2:
377
8f Ley SV.
Baxendale IR.
Brusotti G.
Caldarelli M.
Massi A.
Nesi M.
Farmaco
2002,
57:
321
8g Ley SV.
Baxendale IR.
Nat. Rev. Drug
Discovery
2002,
1:
573
8h Ley SV.
Baxendale IR.
Bream RN.
Jackson PS.
Leach AG.
Longbottom DA.
Nesi M.
Scott JS.
Storer RI.
Taylor SJ.
J. Chem. Soc., Perkin Trans. 1
2000,
3815
8i Baxendale IR.
Ley SV.
Bioorg.
Med. Chem. Lett.
2000,
10:
1983
8j Kirschning A.
Wittenberg R.
Monenschein H.
Chem.-Eur.
J.
2000,
6:
4445
8k Flynn DL.
Devraj RV.
Parlow JJ.
Curr. Opin. Drug Discovery Dev.
1998,
1:
41
8l Flynn DL.
Crich JZ.
Devraj RV.
Hockerman SL.
Parlow JJ.
South MS.
Woodard SS.
J.
Am. Chem. Soc.
1997,
119:
4874
8m Kaldor SW.
Siegel MG.
Fritz JE.
Dressmann
BA.
Hahn PJ.
Tetrahedron Lett.
1996,
37:
7193
8n Booth RJ.
Hodges JC.
J.
Am. Chem. Soc.
1997,
119:
4882
8o Kaldor SW.
Fritz JE.
Tang J.
McKinney ER.
Bioorg.
Med. Chem. Lett.
1996,
6:
3041
9 PS-BEMP refers to 2-tert -butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine
on polystyrene 2% DVB, loading 2.2 mmol/g. Commercially
available from Aldrich Cat No. 20026-XXG where XX is the quantity
in grams.
10 PS-TBD refers to 1,5,7-triazabicyclo[4.4.0]dec-5-ene-polystyrene
cross-linked with 2% DVB, loading 1.33 mmol/g.
Commercially available from Biotage Cat. No. 800422.
11 Available from Varian Inc. named as
Bond Elut silica packed cartridges.
12 Fornicola RS.
Oblinger E.
Montgomery J.
J.
Org. Chem.
1998,
63:
3528
13 Experiments to try and exclude the
possibility of excess ethyl chloroformate being responsible for
the secondary products following addition to the nitrostyrene were conducted
using sub-stoichiometric quantities to quench the original TosMIC
anion. These reactions gave comparable crude mixtures accompanied
by the components from the standard Barton-Zard condensation.
The possibility that the TosMIC could still act as a leaving group
and consequently as an ethyl formate transfer agent can still not
be excluded.
14 The reaction between the lithio enolate 4 and ethyl acrylate gave only a mixture
of products from which only 7% of a rearrangement product
(ethyl 5-tosylpyrrole-1H -3-carboxylate)
could be isolated. ¹ H NMR and X-ray analysis was
used to confirm the structure.
