Three-Component Coupling Synthesis of Diversely Substituted N-Aryl Pyrroles Catalyzed by Iron(III) Chloride

REFERENCES

• Fan , H. ; Peng , J. ; Hamann , M. T. ; Hu , J.-F. Lamellarins and related pyrrole-derived alkaloids from marine organisms . Chem. Rev. 2008 , 108 , 264 – 287 .
   PubMed Web of Science ®Google Scholar
• (a) Kidwai , M. ; Venkataramanan , R. ; Mohan , R. ; Sapra , P. Cancer chemotherapy and heterocyclic compounds . Curr. Med. Chem. 2002 , 9 , 1209 – 1228 ; (b) Bode , H. B. ; Irschik , H. ; Wenzel , S. C. ; Reichenbach , H. ; Mueller , R. ; Hoefle , G. The leupyrrins: A structurally unique family of secondary metabolites from the myxobacterium sorangium cellulosum . J. Nat. Prod. 2003 , 66 , 1203 – 1206 ; (c) Huffman , J. W. ; Padgett , L. W. Recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles, and indenes . Curr. Med. Chem. 2005 , 12 , 1395 – 1411 .
   PubMed Web of Science ®Google Scholar
• Higgins , S. J. Conjugated polymers incorporating pendant functional groups—Synthesis and characterisation . Chem. Soc. Rev. 1997 , 26 , 247 – 257 .
   Web of Science ®Google Scholar
• (a) Biava , M. ; Rossella , F. ; Giulio , C. P. ; Delia , D. ; Carlo , M. ; Pompei , R. 2-Naphthylcarbapenems: Broad-spectrum antibiotics with enhanced potency against MRSA . Bioorg. Med. Chem. Lett. 1999 , 9 , 2893 – 2988 ; (b) Sorokina , I. K. ; Andreeva , N. I. ; Golovina , S. M. Synthesis and anticonvulsant activity of 3-dimethylaminomethyl-8-oxoindeno-[2,1-b]pyrroles . Pharm. Chem. J. 1989 , 23 , 975 – 977 .
   PubMed Web of Science ®Google Scholar
• Carson , J. R. ; Carmosin , R. J. ; Pitis , P. M. ; Vaught , J. L. ; Almond , H. R. ; Stables , J. P. ; Wolf , H. H. ; Swinyard , E. A. ; White , H. S. Aroyl(aminoacyl)pyrroles, a new class of anticonvulsant agents . J. Med. Chem. 1997 , 40 , 1578 .
   PubMed Web of Science ®Google Scholar
• Maria , T. C. ; Cenzo , C. Valentina , O. Synthesis and in vitro antitumoral activity of new N-phenyl-3- pyrrolecarbothioamides . Bioorg. Med. Chem. 2003 , 11 , 495 – 503 .
   PubMed Web of Science ®Google Scholar
• Shibo , J. ; Hong , L. ; Shuwen , L. ; Qian , Z. ; Yuxian H. ; Asim , K. N-Substituted pyrrole derivatives as novel human immunodeficiency virus type 1 entry inhibitors that interfere with the gp41 six-helix bundle formation and block virus fusion . Antimicrob Agents Chemother. 2004 , 48 , 4349 – 4359 .
   PubMed Web of Science ®Google Scholar
• (a) Malinka , W. ; Dziuba , M. S. ; Rajtar , G. ; Rubaj , A. ; Kleinrok , Z. Synthesis and pharmacological screening of some N-(4-substituted-piperazin-1-ylalkyl)-3,4-pyrroledicarboximides . Farmaco 1999 , 54 , 390 – 401 ; (b) Malinka , W. ; Kaczmarz , M. ; Redzicka , A. ; Filipek , B. ; Sapa , J. Synthesis and analgesic action of N-(substituted-ethyl)pyrrole-3,4-dicarboximides . Farmaco 2005 , 60 , 15 – 22 .
   PubMedGoogle Scholar
• (a) Hwang , S. J. ; Cho , S. H. ; Chang , S. Synthesis of condensed pyrroloindoles via Pd-catalyzed intramolecular C-H bond functionalization of pyrroles . J. Am. Chem. Soc. 2008 , 130 , 16158 – 16159 , and reference cited therein .
   PubMed Web of Science ®Google Scholar
• Gallopini , E. Linkers for anchoring sensitizers to semiconductor nanoparticles . Coord. Chem. Rev. 2004 , 248 , 1283 – 1297 .
   Web of Science ®Google Scholar
• (a) Banik , B. K. ; Samajder , S. ; Banik , I. Simple synthesis of substituted pyrroles. J. Org. Chem. 2004, 69, 213–216, and reference cited therein; (b) Biavaa , M. ; Porrettaa , G. C. ; Giorgia , G. ; Sleiterb , G. β-Aminomethylation of N-aryl and N-azaheteroaryl-substituted methyl 2,5-dimethylpyrrole-3-carboxylates: Kinetic effect of the N-pyrrole substituent. Arkivoc 2004, 325–333.
   PubMed Web of Science ®Google Scholar
• (a) Kim , A. Y. ; Lee , H. J. ; Park , J. C. ; Kang , H. ; Yang , H. ; Song , H. ; Park , K. H. Highly efficient and reusable copper-catalyzed N-arylation of nitrogen-containing heterocycles with aryl halides . Molecules 2009 , 14 , 5169 – 5178 ; (b) Klapars , A. ; Antilla , J. C. ; Huang , X. ; Buchwald , S. L. A general and efficient copper catalyst for the amidation of aryl halides and the N-arylation of nitrogen heterocycles . J. Am. Chem. Soc. 2001 , 123 , 7727 – 7729 ; (c) Ma , H.-C. ; Jiang , X.-Z. N-Hydroxyimides as efficient ligands for the copper-catalyzed N-arylation of pyrrole, imidazole, and indole . J. Org. Chem. 2007 , 72 , 8943 – 8946 , and reference cited therein ; (d) Antilla , J. C. ; Baskin , J. M. ; Barder T. E. ; Buchwald , S. L. Copper-diamine-catalyzed N-arylation of pyrroles, pyrazoles, indazoles, imidazoles, and triazoles . J. Org. Chem. 2004 , 69 , 5578 – 5587 .
   PubMedGoogle Scholar
• Yu , S. ; Saenz , J. Srirangam , J. K. Facile synthesis of N-aryl pyrroles via Cu(II)-mediated cross coupling of electron-deficient pyrroles and arylboronic acids . J. Org. Chem. 2002 , 67 , 1699 – 1702 .
   PubMed Web of Science ®Google Scholar
• Liao , Q. ; Zhang , L. ; Wang , F. ; Li , S. ; Xi , C. Copper-catalyzed double N-vinylation of aromatic amines: An efficient synthesis of various substituted N-arylpyrroles . Eur. J. Org. Chem. 2010 , 1 , 5426 – 5431 .
   Google Scholar
• Yan , R.-L. ; Luo , J. ; Wang , C.-X. ; Ma , C.-W. ; Huang , G.-S. ; Liang , Y.-M. Cu(I)-catalyzed synthesis of polysubstituted pyrroles from dialkyl ethylenedicarboxylates and β-enamino ketones or esters in the presence of O2 . J. Org. Chem. 2010 , 75 , 5395 – 5397 .
   PubMed Web of Science ®Google Scholar
• Galliford , C. V. ; Scheidt , K. A. Catalytic multicomponent reactions for the synthesis of N-Aryl trisubstituted pyrroles . J. Org. Chem. 2007 , 72 , 1811 – 1813 .
   PubMed Web of Science ®Google Scholar
• Liu , X.-T. ; Hao , L. ; Lin , M. ; Chen , L. Zhan , Z.-P. One-pot highly efficient synthesis of substituted pyrroles and N-bridgehead pyrroles by zinc-catalyzed multicomponent reaction . Org. Biomol. Chem. 2010 , 8 , 3064 – 3072 .
   PubMed Web of Science ®Google Scholar
• Bian , Y.-J. ; Liu , X.-Y. ; Ji , K.-G. ; Shu , X.-Z. ; Guo , L.-N. ; Liang , Y.-M. Efficient synthesis of highly substituted pyrroles based on the tandem reactions: Intermolecular amination and Pd(II)-catalyzed intramolecular hydroamidation . Tetrahedron 2009 , 65 , 1424 – 1429 .
   Web of Science ®Google Scholar
• (a) For a recent review, see , Estévez , V. ; Villacampa , M. ; Menéndez , J. C. Multicomponent reactions for the synthesis of pyrroles . Chem. Soc. Rev. 2010 , 39 , 4402 – 4421 , and references cited therein ; (b) Balme , G. Pyrrole synthesis by multicomponent coupling reactions . Angew. Chem. Int. Ed. 2004 , 43 , 6238 – 6241 ; (c) Maiti , S. ; Biswas , S. ; Jana , U. Iron(III)-catalyzed four-component coupling reaction of 1,3-dicarbonyl compounds, amines, aldehydes, and nitroalkanes: A simple and direct synthesis of functionalized pyrroles . J. Org. Chem. 2010 , 75 , 1674 – 1683 , and references cited therein .
   PubMed Web of Science ®Google Scholar
• (a) Jana , U. ; Maiti , S. ; Biswas , S. An FeCl3-catalyzed highly C3-selective Friedel–Crafts alkylation of indoles with alcohols . Tetrahedron Lett. 2007 , 48 , 7160 – 7163 ; (b) Bera , K. ; Sarkar , S. ; Biswas , S. ; Maiti , S. ; Jana , U. Iron-catalyzed synthesis of functionalized 2H-chromenes via intramolecular alkyne carbonyl metathesis . J. Org. Chem. 2011 , 76 , 3539 – 3544 .
   Web of Science ®Google Scholar
• (a) Meyer , H. Heterocyclen aus Nitroalkenen, I: Pyrrole durch cyclisierende Michael addition von Enaminen . Liebigs Ann. Chem. 1981 , 1534 – 1544 ; (b) Shiraishi , H. ; Nishitani , T. ; Sakaguchi , S. ; Ishii , Y. Preparation of substituted alkylpyrroles via samarium-catalyzed three-component coupling reaction of aldehydes, amines, and nitroalkanes . J. Org. Chem. 1998 , 63 , 6234 – 6238 ; (c) Ranu , B. C. , Hajra , A. ; Jana , U. Microwave-assisted synthesis of substituted pyrroles by a three-component coupling of α, β-unsaturated carbonyl compounds, aliphatic amines, and nitroalkanes on the surface of silica gel . Synlett 2000 , 75 ; (d) Alizadeh , A. ; Rezvanian , A. ; Bijanzadeh , H. R. synthesis of highly functionalized pyrrole derivatives via a four-component reaction of two primary amines and diketene in the presence of nitrostyrene . Synthesis 2008 , 725 – 728 .
   Google Scholar