Abstract
A simple and facile preparation of chiral and bis-pyrroles is described here. This method involves a modified Paal-Knorr reaction using 1,4-dicarbonyl systems derived from ozonolysis of allylated β-ketoester.
Key words
Paal-Knorr synthesis - chiral and bispyrroles - ozonolysis - allylated β-ketoester
References
For recent reviews, see:
1a
Reddy GM.
Bhavani AKD.
Reddy PP.
Reddy PSN.
Synthesis
2002,
1311
1b
Ferreira VF.
de Souza MCBV.
Cunha AC.
Pereira LOR.
Ferreira MLG.
Organic Preparations and Procedures Int.
2001,
33:
411
1c
Korostova SE.
Mikhaleva AI.
Vasil’tsov AM.
Trofimov BA.
Russ. J. Org. Chem.
1998,
34:
911
1d
Korostova SE.
Mikhaleva AI.
Vasil’tsov AM.
Trofimov BA.
Russ. J. Org. Chem.
1998,
34:
1691
2a
Tourillon G. In
Handbook of Conducting Polymers
Vol. 1:
Skotheim TA.
Dekker;
New York:
1986.
p.294-351
2b
Street GB. In
Handbook of Conducting Polymers
Vol. 1:
Skotheim TA.
Dekker;
New York:
1986.
p.265-294
3 For a review on pyrrolizidines, see: Yamashita T.
Yasuda K.
Kizu H.
Kameda Y.
Watson AA.
Nash RJ.
Fleet GWJ.
Asano N.
J. Nat. Prod.
2002,
45:
1875
For reviews on Knorr pyrrole synthesis, see:
4a
Knorr L.
Chem. Ber.
1884,
17:
546
4b
Knorr L.
Justus Liebig Ann. Chem.
1886,
236:
290
4c
Davies DT. In
Aromatic Heterocyclic Chemistry
Oxford;
New York, NY:
1992.
p.10
4d
Gilchrist TL. In
Heterocyclic Chemistry
John Wiley and Sons;
New York, NY:
1992.
p.188
For recent examples of Knorr pyrrole synthesis, see:
5a
Calvo L.
González-Ortega A.
Sañudo MC.
Synthesis
2002,
2450
5b
Danks TN.
Tetrahedron Lett.
1999,
40:
3957
6 For a review on Paal-Knorr pyrrole synthesis, see: Katrizky AR. In
Handbook of Heterocyclic Chemistry
1st ed:
Pergamon Press;
New York, NY:
1985.
For recent examples of Paal-Knorr pyrrole synthesis, see:
7a
Agami C.
Dechoux L.
Hamon L.
Hebbe S.
Synthesis
2003,
6:
859
7b
Quiclet-Sire B.
Quintero L.
Sanchez-Jimenez G.
Zard SZ.
Synlett
2003,
75
7c
Raghavan S.
Anuradha K.
Synlett
2003,
5:
711
7d
Curini M.
Montanari F.
Rosati O.
Lioy E.
Margarita R.
Tetrahedron Lett.
2003,
44:
3923
7e
Baxendale IR.
Brusotti G.
Matsuoka M.
Ley SV.
J. Chem. Soc., Perkin Trans. 1
2002,
143
7f
Friedrich M.
Wächtler A.
de Meijere A.
Synlett
2002,
4:
619
7g
Ferreira PMT.
Maia HLS.
Monteiro LS.
Tetrahedron Lett.
2002,
43:
4491
7h
Hewton CE.
Kimber MC.
Taylor DK.
Tetrahedron Lett.
2002,
43:
3199
7i
Braun RU.
Zeitler K.
Muller TJJ.
Org. Lett.
2001,
3:
3297
7j
Rao HSP.
Jothilingam S.
Tetrahedron Lett.
2001,
42:
6595
7k
Chen N.
Lu Y.
Gadamasetti K.
Hurt CR.
Norman MH.
Fotsch C.
J. Org. Chem.
2000,
65:
2603
7l
Xu G.
Liu Y.
Sayre LM.
J. Org. Chem.
1999,
64:
5732
For Hantzsch pyrrole synthesis, see:
8a
Hantzsch A.
Chem. Ber.
1890,
23:
1474
8b A recent example, see: Palacios F.
Aparicio D.
de los Santos JM.
Vicario J.
Tetrahedron
2001,
57:
1961
For recent preparations of chiral pyrroles, see:
9a
Settambolo R.
Guazzelli G.
Mengali L.
Mandoli A.
Lazzaroni R.
Tetrahedron: Asymmetry
2003,
14:
2491
9b
Wasserman HH.
Long YO.
Zhang R.
Carr AJ.
Parr J.
Tetrahedron Lett.
2002,
43:
3347
9c
Ong CW.
Chen CM.
Wang LH.
Jan JJ.
J. Org. Chem.
1998,
63:
9131
9d
Grigg R.
Yoganathan G.
Tetrahedron: Asymmetry
1996,
7:
273
For recent preparations of bispyrroles, see:
10a
Bröring M.
Link S.
Synthesis
2002,
1:
67
10b
Wasserman HH.
Long YO.
Zhang R.
Carr AJ.
Parr J.
Tetrahedron Lett.
2002,
43:
3347
10c
Chacon-Garciá L.
Martinez R.
Eur. J. Med. Chem.
2002,
37:
261
10d
Just PE.
Chane-Ching KI.
Lacaze PC.
Tetrahedron
2002,
58:
3467
10e
Domingo VM.
Alemán C.
Brillas E.
Juliá L.
J. Org. Chem.
2001,
66:
4058
10f
Attanasi OA.
Crescentini LD.
Filippone P.
Perrulli FR.
Santeusanio S.
Synlett
1999,
339
10g For some earliest preparations of bispyrroles, see the following: Buu-Hoï NP.
Xuong N.
J. Org. Chem.
1955,
20:
850
10h
Adams R.
Joyce RM.
J. Am. Chem. Soc.
1938,
60:
1491
10i
Chang C.
Joyce RM.
J. Am. Chem. Soc.
1934,
56:
2089
For recent examples on transition metal-mediated methods for the pyrrole synthesis, see:
11a
Gabriele B.
Salerno G.
Fazio A.
J. Org. Chem.
2003,
68:
7853
11b
Zhang Y.
Herdon JW.
Org. Lett.
2003,
5:
2043
11c
Nakano H.
Ishibashi T.
Sawada T.
Tetrahedron Lett.
2003,
44:
4175
11d
Takaya H.
Kojima S.
Murahashi S.-I.
Org. Lett.
2001,
3:
421
11e
Kel’in AV.
Sromek AW.
Gevorgyan V.
J. Am. Chem. Soc.
2001,
123:
2074
11f
Farcas S.
Namy J.-L.
Tetrahedron
2001,
57:
4881
11g
Gabriele B.
Salerno G.
Fazio A.
Bossio MR.
Tetrahedron Lett.
2001,
44:
1339
11h
Lee C.-F.
Yang L.-M.
Hwu T.-Y.
Feng A.-S.
Tseng J.-C.
Luh T.-Y.
J. Am. Chem. Soc.
2000,
122:
4992
11i
Grigg R.
Savic V.
Chem. Commun.
2000,
873
11j
Dieter RK.
Yu H.
Org. Lett.
2000,
2:
2283
For other related preparations of pyrroles, see:
12a
Ranu BC.
Dey SS.
Tetrahedron Lett.
2003,
44:
2865
12b
Ranu BC.
Hajra A.
Tetrahedron
2001,
57:
4767
12c
Lagu B.
Pan M.
Wachter MP.
Tetrahedron Lett.
2001,
42:
6027
12d
Bullington JL.
Wolff RR.
Jackson PF.
J. Org. Chem.
2002,
67:
9439
12e
Quiclet-Sire B.
Wendeborn F.
Zard SZ.
Chem. Commun.
2002,
2214
12f
Aelterman W.
De Kimpe N.
Tyvorskii V.
Kulinkovich O.
J. Org. Chem.
2001,
66:
53-58
12g
Katrizky AR.
Huang T.-B.
Voronkov MV.
Wang M.
Kolb H.
J. Org. Chem.
2000,
65:
8819
12h
Simoni D.
Rondanin R.
Furnò G.
Aiello E.
Invidiata FP.
Tetrahedron Lett.
2000,
41:
2699
For some examples, see:
13a
Molander GA.
Cameron KOJ.
J. Am. Chem. Soc.
1993,
115:
830
13b
Amarnath V.
Amarnath K.
Valentine WM.
Eng MA.
Graham DG.
Chem. Res. Toxicol.
1995,
8:
234
13c
Xu G.
Sayre LM.
Chem. Res. Toxicol.
1999,
12:
862
14 Solvents such as MeOH, CH3 CN, THF, EtOAc, CH2 Cl2 , and toluene were screened with CH3 CN giving the highest yield and cleanest products as determined by LCMS. The reactions were also run at r.t., 50 °C, and 80 °C to determine the optimal temperature. A variety of acids such as aq HCl and aq H2 SO4 were screened in addition to p -TsOH.