Abstract
1H -Pyrroles were converted into 1,4-dicarbonyl compounds, and then into 1H -pyrroles with a different N-substituent by heating at 110 °C under nitrogen in 0.3 M sodium citrate buffer, pH 3, and in the presence of alkyl or aryl amines. The new pyrroles were obtained in low to very high yields depending upon the pH, the reaction time, the initial pyrrole and amine involved, and the proportion between both reagents.
Key words
amines - cyclizations - pyrroles - ring-closure reactions - ring-opening reactions
References and Notes
1a
Knorr L.
Ber. Dtsch. Chem. Ges.
1884,
17:
1635
1b
Paal C.
Ber. Dtsch. Chem. Ges.
1885,
18:
367
1c
Banik BK.
Samajdar S.
Banik I.
J. Org. Chem.
2004,
69:
213
1d
Banik BK.
Banik I.
Renteria M.
Dasgupta SK.
Tetrahedon Lett.
2005,
46:
2643
1e
Werner S.
Iyer PS.
Synlett
2005,
1405
2a
Hidalgo FJ.
Zamora R.
J. Biol. Chem.
1993,
268:
16190
2b
Hidalgo FJ.
Zamora R.
J. Lipid Res.
1995,
36:
725
2c
Lee SH.
Oe T.
Blair IA.
Chem. Res. Toxicol.
2002,
15:
300
2d
Zamora R.
Hidalgo FJ.
Chem. Res. Toxicol.
2003,
16:
1632
2e
Zamora R.
Hidalgo FJ.
Chem. Res. Toxicol.
2005,
18:
342
3a
Sayre LM.
Arora PK.
Iyer RS.
Salomon RG.
Chem. Res. Toxicol.
1993,
6:
19
3b
Sayre LM.
Sha W.
Xu G.
Kaur K.
Nadkarni D.
Subbanagounder G.
Salomon RG.
Chem. Res. Toxicol.
1996,
9:
1194
3c
Amarnath V.
Valentine WN.
Montine TJ.
Patterson WH.
Amarnath K.
Basset CN.
Grahan DG.
Chem. Res. Toxicol.
1998,
11:
317
3d
Liu Z.
Minkler PE.
Sayre LM.
Chem. Res. Toxicol.
2003,
16:
901
4a
Buu-Hoi NP.
Xuong ND.
J. Org. Chem.
1955,
20:
850
4b
Danks TN.
Tetrahedron Lett.
1999,
40:
3957
4c
Quiclet-Sire B.
Quintero L.
Sanchez-Jimenez G.
Zard SZ.
Synlett
2003,
75
4d
Wang B.
Gu Y.
Luo C.
Yang T.
Yang L.
Suo J.
Tetrahedron Lett.
2004,
45:
3417
5a
Katritzky AR.
Karelson M.
Malhotra N.
Heterocycles
1991,
32:
127
5b
Nyulaszi L.
Varnai P.
Veszpremi T.
J. Mol. Struct. (THEOCHEM)
1995,
358:
55
6 Reactions were carried out by heating at 110 °C under an inert atmosphere, the pyrrole (0.1 mmol) in 3 mL of 0.3 M sodium citrate buffer (pH 3), and in the presence, or not, of the amine (0.1 mmol). The pyrroles produced were extracted three times with CHCl3 -MeOH (3:2) and purified by TLC. Identity of purified compounds was confirmed by 1 H NMR, 13 C NMR and MS.
7
Hargis DC.
Shubkin RL.
Tetrahedron Lett.
1990,
31:
2991
8a
Ledl F.
Schleicher E.
Angew. Chem., Int. Ed. Engl.
1990,
19:
565
8b
Hidalgo FJ.
Zamora R.
Chem. Res. Toxicol.
2000,
13:
501
8c
Salomon RG.
Kaur K.
Podrez E.
Hoff HF.
Krushinsky AV.
Sayre LM.
Chem. Res. Toxicol.
2000,
13:
557
8d
Hidalgo FJ.
Zamora R.
Ann. N.Y. Acad. Sci.
2005,
1043:
319
9a
Zamora R.
Hidalgo FJ.
J. Agric. Food Chem.
2001,
48:
6006
9b
Powell SR.
Wang P.
Divald A.
Teichberg S.
Haridas V.
McCloskey TW.
Davies KJA.
Hartzeff H.
Free Radical Biol. Med.
2005,
38:
1093
10a
Steinbrecher UP.
Lougheed M.
Kwan WC.
Dirks M.
J. Biol. Chem.
1989,
264:
15216
10b
Podrez EA.
Hoppe G.
O’Neil J.
Sayre LM.
Sheibani N.
Hoff HF.
J. Lipid Res.
2000,
41:
1455
10c
Stocker R.
Keaney JF.
Physiol. Rev.
2004,
84:
1381
11a
Hidalgo FJ.
Alaiz M.
Zamora R.
Anal. Biochem.
1998,
262:
129
11b
Gu X.
Meer SG.
Miyagi M.
Rayborn ME.
Hollyfield JG.
Crabb JW.
Salomon RG.
J. Biol. Chem.
2003,
278:
42027
11c
Hidalgo FJ.
Nogales F.
Zamora R.
Anal. Biochem.
2004,
334:
155