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Synlett 2009(14): 2245-2248  
DOI: 10.1055/s-0029-1217799
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Iron-Catalyzed Inexpensive and Practical Synthesis of N-Substituted Pyrroles in Water

Najmedin Azizi*a, Alireza Khajeh-Amiria, Hossein Ghafurib, Mohammad Bolourtchiana, Mohammad Reza Saidib
a Chemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
Fax: +98(21)44580762; e-Mail: azizi@ccerci.ac.ir;
b Department of Chemistry, Sharif University of Technology, P. O. Box 11465-9516, Tehran 11365, Iran
Further Information

Publication History

Received 27 April 2009
Publication Date:
06 August 2009 (online)

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Abstract

An operationally simple, practical, and economical protocol for iron(III) chloride catalyzed Paal-Knorr pyrrole synthesis in water in good to excellent yields has been developed. Several N-substituted pyrroles are readily prepared from the reaction of 2,5-dimethoxytetrahydrofuran and aryl/alkyl, sulfonyl and acyl amines under very mild reaction conditions

Key words

dimethoxytetrahydrofuran - iron - pyrrole - amine - water chemistry

    References and Notes

  • 1a Li C.-J. Chem. Rev.  2005,  105:  3095 
    Google Scholar
  • 1b Demko ZP. Sharpless KB. J. Org. Chem.  2001,  66:  7945 
    Google Scholar
  • 1c Mitsudome T. Arita S. Mori H. Mizugaki T. Jitsukawa K. Kaneda K. Angew. Chem. Int. Ed.  2008,  47:  7938 
    Google Scholar
  • 1d Hayashi Y. Samanta S. Gotoh H. Ishikawa H. Angew. Chem. Int. Ed.  2008,  47:  6634 
    Google Scholar
  • 2a Jones RA. Bean GP. The Chemistry of Pyrroles   Academic Press; London: 1977. 
    Google Scholar
  • 2b Lipshutz BH. Chem. Rev.  1986,  86:  795 
    Google Scholar
  • 3a Jacobi PA. Coults LD. Guo JS. Leung SI. J. Org. Chem.  2000,  65:  205 
    Google Scholar
  • 3b Fürstner A. Angew. Chem.  2003,  115:  3706 
    Google Scholar
  • 3c Fürstner A. Szillat H. Gabor B. Mynott R. J. Am. Chem. Soc.  1998,  120:  8305 
    Google Scholar
  • 4a Boger DL. Boyce CW. Labrili MA. Sehon CA. Jin Q. J. Am. Chem. Soc.  1999,  121:  54 
    Google Scholar
  • 4b Paolesse R. Nardis S. Sagone F. Khoury RG. J. Org. Chem.  2001,  66:  550 
    Google Scholar
  • 5 Domingo VM. Aleman C. Brillas E. Julia L. J. Org. Chem.  2001,  66:  4058 
    CrossrefPubMedGoogle Scholar
  • 6a St. Cyr DJ. Arndtsen BA. J. Am. Chem. Soc.  2007,  129:  12366 
    Google Scholar
  • 6b Dhawan R. Arndtsen BA. J. Am. Chem. Soc.  2004,  126:  468 
    Google Scholar
  • 6c Kamijo S. Kanazawa C. Yamamoto Y. J. Am. Chem. Soc.  2005,  127:  9260 
    Google Scholar
  • 6d Abid M. Spaeth A. Török B. Adv. Synth. Catal.  2006,  348:  2191 
    Google Scholar
  • 6e Abid M. Teixeira L. Torok B. Org. Lett.  2008,  10:  933 
    Google Scholar
  • 6f Shindo M. Yoshimura Y. Hayashi M. Soejima H. Yoshikawa T. Matsumoto K. Shishido K. Org. Lett.  2007,  9:  1963 
    Google Scholar
  • 6g Chiba S. Wang Y.-F. Lapointe G. Narasaka K. Org. Lett.  2008,  10:  313 
    Google Scholar
  • 6h Veitch GE. Bridgwood K. Rands-Trevor LK. Ley SV. Synlett  2008,  2597 
    Google Scholar
  • 7a Cooney JV. McEwen WE. J. Org. Chem.  1981,  46:  2570 
    Google Scholar
  • 7b Wurtz NR. Turner JM. Baird EE. Dervan PB. Org. Lett.  2001,  3:  1201 
    Google Scholar
  • 7c Ballini R. Bosica G. Fiorini G. Giarlo G. Synthesis  2001,  2003 
    Google Scholar
  • 7d Arrowsmith J. Jennings SA. Clark AS. Stevens MFG. J. Med. Chem.  2002,  45:  5458 
    Google Scholar
  • 7e Bartolo G. Salerno G. Fazio A. J. Org. Chem.  2003,  68:  7853 ; and references therein
    Google Scholar
  • 7f Trost BM. Doherty GA. J. Am. Chem. Soc.  2000,  122:  3801 
    Google Scholar
  • 7g Tracey MR. Hsung RP. Lambeth RH. Synthesis  2004,  918 
    Google Scholar
  • 8a Yu SX. Quesne PWL. Tetrahedron Lett.  1995,  36:  6205 
    Google Scholar
  • 8b Yadav JS. Reddy BVS. Eeshwaraiah B. Gupta MK. Tetrahedron Lett.  2004,  45:  5873 
    Google Scholar
  • 8c Braun RU. Zeitler K. Müller TJJ. Org. Lett.  2001,  3:  3297 
    Google Scholar
  • 8d Curini M. Montanari F. Rosati O. Lioy E. Margarita R. Tetrahedron Lett.  2003,  44:  3923 
    Google Scholar
  • 8e Banik BK. Samajdar S. Banik I. J. Org. Chem.  2004,  69:  213 
    Google Scholar
  • 8f Balme G. Angew. Chem. Int. Ed.  2004,  43:  6238 
    Google Scholar
  • 8g Bharadwaj AR. Scheidt KA. Org. Lett.  2004,  6:  2465 
    Google Scholar
  • 8h Ballini R. Barboni L. Bosica G. Petrini M. Synlett  2000,  391 
    Google Scholar
  • 8i Minetto G. Raveglia LF. Sega A. Taddei M. Eur. J. Org. Chem.  2005,  70:  5277 
    Google Scholar
  • 8j Raghavan S. Anuradha K. Synlett  2003,  711 
    Google Scholar
  • 8k Quiclet-Sire B. Quintero L. Sanchez-Jimenez G. Zard Z. Synlett  2003,  75 
    Google Scholar
  • 9a Chen J. Wu H. Zheng Z. Jin C. Zhang X. Su W. Tetrahedron Lett.  2006,  47:  5383 
    Google Scholar
  • 9b Banik BK. Banik I. Renteria M. Dasgupta SK. Tetrahedron Lett.  2005,  46:  2643 
    Google Scholar
  • 9c Ooi T. Ohmatsu K. Ishii H. Saito A. Maruoka K. Tetrahedron Lett.  2004,  45:  9315 
    Google Scholar
  • 9d Wang B. Gu Y. Luo C. Yang T. Yang L. Suo J. Tetrahedron Lett.  2004,  45:  3417 
    Google Scholar
  • 9e Minetto G. Raveglia LF. Taddei M. Org. Lett.  2004,  6:  389 
    Google Scholar
  • 9f Mamane V. Hannen P. Chem. Eur. J.  2004,  10:  4556 
    Google Scholar
  • 9g Delen Z. Lahti PM. J. Org. Chem.  2006,  71:  934 
    Google Scholar
  • 10a Azizi N. Saidi MR. Eur. J. Org. Chem.  2003,  4630 
    Google Scholar
  • 10b Azizi N. Saidi MR. Tetrahedron  2004,  60:  383 
    Google Scholar
  • 10c Azizi N. Saidi MR. Organometallics  2004,  23:  1457 
    Google Scholar
  • 10d Azizi N. Saidi MR. Org. Lett.  2005,  7:  3649 
    Google Scholar
  • 10e Azizi N. Aryanasab F. Torkiyan L. Ziyaei A. Saidi MR. J. Org. Chem.  2006,  71:  3634 
    Google Scholar
  • 10f Azizi N. Torkiyan L. Saidi MR. Org. Lett.  2006,  8:  2079 
    Google Scholar
  • 10g Azizi N. Aryanasab F. Saidi MR. Org. Biomol. Chem.  2006,  4:  4275 
    Google Scholar
  • 11 Jolicoeur B. Chapman EE. Thompson A. Lubell WD. Tetrahedron  2006,  62:  11531 ; and references cited therein
    CrossrefGoogle Scholar
  • 12 Abid M. Teixeira L. Török B. Tetrahedron Lett.  2007,  48:  4047 
    CrossrefGoogle Scholar
  • 13a Yuan X. Xu X. Zhou X. Yuan J. Mai L. Li Y. J. Org. Chem.  2007,  72:  1510 
    Google Scholar
  • 13b Li JJ. Name Reactions in Heterocyclic Chemistry   Corey EJ. Wiley and Sons; New York: 2005.  p.Chap. 2 
    Google Scholar
  • 14 Lea ZG. Chen ZC. Hu Y. Zheng QG. Synthesis  2004,  1951 ; and references cited therein
    Article in Thieme ConnectGoogle Scholar
  • 15a Gross H. Chem. Ber.  1962,  95:  2270 
    Google Scholar
  • 15b Elming N. Clauson-Kass N. Acta Chem. Scand.  1952,  6:  867 
    Google Scholar
  • 16a Fang Y. Leysen D. Ottenheijm HCJ. Synth. Commun.  1995,  25:  1857 
    Google Scholar
  • 16b Ekkati AR. Bates DK. Synthesis  2003,  1959 
    Google Scholar
17

General Procedure for the Synthesis of Pyrroles in Water To a mixture of the amine (5 mmol) and 2,5 dimethoxy-tetrahydrofuran (6 mmol) in H2O (4 mL) at 60 ˚C FeCl3˙7H2O (2 mol%) was added. The mixture was stirred at this temperature for 1-4 h and was diluted with EtOAc and filtered. The organic solution was evaporated under vacuum affording the pyrrole derivative with good analytical purity. In the few cases, the crude product was purified by flash chromatography.