A Simple and Efficient Metal-Free Synthesis of Tetrasubstituted Pyrroles by Iodine-Catalyzed Four-Component Coupling Reaction of Aldehydes, Amines, Dialkyl Acetylenedicarboxylates, and Nitromethane [¹]

Abstract

The four-component coupling reaction of aldehydes, amines, dialkyl acetylenedicarboxylates, and nitromethane in the presence of molecular iodine as a catalyst furnished the corresponding 1,2,3,4-tetrasubstituted pyrroles under reflux. The products are formed in high yields (65-88%) within 8 hours. The method is simple, efficient, cost-effective, and metal-free.

Key words

1,2,3,4-tetrasubstituted pyrroles - four-component coupling reaction - iodine - metal-free synthesis

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Part 230 in the series ‘Studies on Novel Synthetic Methodologies’.

References

• 2a Denny WA. Rewcastle GW. Baguley BC. J. Med. Chem.  1990,  33:  814 
• 2b Daidone G. Maggis B. Schillari D. Pharmazie  1990,  45:  441 
• 2c Davis FA. Bowen KA. Xu H. Velvadapu V. Tetrahedron  2008,  64:  4174 
• 3a O’Hagan D. Nat. Prod. Rep.  2000,  17:  435 
• 3b Walsh CT. Gameau-Tsodikova S. Howard-Jones AR. Nat. Prod. Rep.  2006,  23:  517 
• 3c Reisser M. Maas G. J. Org. Chem.  2008,  69:  4913 
• 4a Boger DL. Boyce CW. Labrilli MA. Sehon CA. Jin Q. J. Am. Chem. Soc.  1999,  121:  54 
• 4b Abid M. Landge SM. Torok B. Org. Prep. Proced. Int.  2006,  38:  495 
• 5a Ramanavicius A. Ramanaviciene A. Malinauskas A. Electrochem. Acta  2006,  51:  6025 
• 5b Pu S. Liu G. Shen L. Xu J. Org. Lett.  2007,  9:  2139 
• Some recent examples:
• 6a Shiner CM. Taner TD. Tetrahedron  2005,  61:  11628 
• 6b Minetto G. Raveglia LF. Sega A. Taddei M. Eur. J. Org. Chem.  2005,  34:  5277 
• 6c Larionov OV. de Meijire A. Angew. Chem. Int. Ed.  2005,  44:  5664 
• 6d Istrate FM. Gagosz F. Org. Lett.  2007,  9:  318 
• 6e Hwang SJ. Cho SH. Chang S. J. Am. Chem. Soc.  2008,  130:  16158 
• 6f La YD. Arndtsen BA. Angew. Chem. Int. Ed.  2008,  47:  5430 
• 6g Plaskon AS. Ryabukhin SV. Volochnyuk DM. Shivanyuk AN. Tolmachev AA. Tetrahedron  2008,  64:  5933 
• 6h Alizadeh A. Rezvanian A. Bijanzadeh HR. Synthesis  2008,  725 
• 6i Brichacek M. Njardarson JT. Org. Biomol. Chem.  2009,  7:  1760 
• 6j Lu Y. Fu X. Chen H. Du X. Jia X. Liu Y. Adv. Synth. Catal.  2009,  351:  129 
• 6k Wang J.-Y. Wang X.-P. Yu Z.-S. Yu W. Adv. Synth. Catal.  2009,  351:  2063 
• 7a Das B. Ramu R. Reddy MR. Mahender G. Synthesis  2005,  250 
• 7b Das B. Krishnaiah M. Venkateswarlu K. Tetrahedron Lett.  2006,  47:  4457 
• 7c Das B. Damodar K. Bhunia N. J. Org. Chem.  2009,  74:  5607 
• 7d Das B. Reddy GC. Balasubramanyam P. Veeranjaneyulu B. Synthesis  2010,  1625 

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Part 230 in the series ‘Studies on Novel Synthetic Methodologies’.