Palladium-Catalyzed N-Arylation of 3-Functionalized 2-Amino-4,5-dimethylpyrroles

REFERENCES

• Roth , H. J. ; Eger , K. Synthese von 2-amino-3-cyano-pyrrolen . Arch. Pharm. 1975 , 308 , 179 – 185 .
   PubMed Web of Science ®Google Scholar
• Mattson , R. J. ; Wang , L.-C. ; Sowell , J. W. Synthesis of substituted 2-amino-3-(alkyl or aryl)sulfonylpyrroles . J. Heterocycl. Chem. 1980 , 17 , 1793 – 1795 .
   Web of Science ®Google Scholar
• Laks , J. S. ; Ross , J. R. ; Bayomi , S. M. ; Sowell , J. W. Synthesis of N-1-substituted 2-amino-3-t-butoxycarbonyl-4,5-dimethylpyrroles . Synthesis 1985 , 291 – 293 .
   Google Scholar
• Vishwakarma , L. C. ; Sowell , J. W. Synthesis of 4,7-dihydro-4-oxopyrrolo[2,3-b]pyridine-5-carboxylic acid derivatives as potential antimicrobial agents . J. Heterocycl. Chem. 1985 , 22 , 1429 – 1433 .
   Google Scholar
• Traxler , P. M. ; Furet , P. ; Mett , H. ; Buchdunger , E. ; Meyer , T. ; Lydon , N. 4-(Phenylamino)pyrrolopyrimidines: Potent and selective, ATP site directed inhibitors of the EGF-receptor protein tyrosine kinase . J. Med. Chem. 1996 , 39 , 2285 – 2292 .
   PubMed Web of Science ®Google Scholar
• Bayomi , S. M. ; Haddad , D. Y. ; Sowell , J. W. One-step synthesis of 6,7-dimethyl-2-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a][1,3]pyrimidines . J. Heterocycl. Chem. 1984 , 21 , 1367 – 1368 .
   Google Scholar
• Ross , J. R. ; Laks , J. S. ; Wang , D. L.-C. ; Sowell , J. W. Synthesis of 7-substituted 5,6-dimethyl-2,4-dioxo-1,2,4,7-tetrahydropyrrolo[2,3-d][1,3]oxazines . Synthesis 1985 , 796 – 798 .
   Google Scholar
• Wang , D. L. ; Bayomi , S. M. ; Sowell , J. W. Synthesis of substituted pyrrolo[3,2-b][1,4]thiazine 1,1-dioxides . Pakistan J. Sci. Ind. Res. 1988 , 31 , 242 – 244 .
   Google Scholar
• Stephens , C. E. ; Sowell , J. W. Synthesis of substituted pyrrolo[2,3-e][1,3,4]-thiadiazine 4,4-dioxides . J. Heterocycl. Chem. 1996 , 33 , 1615 – 1617 .
   Google Scholar
• Vorob'ev , E. V. ; Kurbatov , E. S. ; Krasnikov , V. V. ; Mezheritskii , V. V. ; Usova , E. V. Synthesis and rearrangement of 7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]- and 7H-pyrrolo[3,2-e][1,2,4]triazolo[4,3-c]pyrimidines . Russ. Chem. Bull., Int. Ed. 2006 , 55 , 1492 – 1497 .
   Google Scholar
• Player , M. R. ; Sowell , J. W. ; Patil , G. S. ; Kam , C.-M. ; Powers , J. C. 1,3-Oxazino[4,5-b]indole-2,4-(1H,9H)-diones and 5,6-dimethylpyrrolo[2,3-d]-1,3-oxazin-2,4-(1H,7H)-diones as serine protease inhibitors . Bioorg. Med. Chem. Lett. 1994 , 4 , 949 – 954 .
   Google Scholar
• Corbet , J.-P. ; Mignani , G. Selected patented cross-coupling reaction technologies. Chem. Rev. 2006, 106, 2651–2710.
   PubMed Web of Science ®Google Scholar
• Buchwald , S. L. ; Mauger , C. ; Mignani , G. ; Scholz , U. Industrial-scale palladium-catalyzed coupling of aryl halides and amines—A personal account . Adv. Synth. Catal. 2006 , 348 , 23 – 39 .
   Web of Science ®Google Scholar
• Harris , M. C. ; Geis , O. ; Buchwald , S. L. Sequential N-arylation of primary amines as a route to alkyldiarylamines . J. Org. Chem. 1999 , 64 , 6019 – 6022 .
   Web of Science ®Google Scholar
• Yin , T. ; Zhao , M. M. ; Huffman , M. A. ; McNamara , J. M. Pd-catalyzed N-arylation of heteroarylamines . Org. Lett. 2002 , 4 , 3481 – 3484 .
   PubMed Web of Science ®Google Scholar
• Anbazhagan , M. ; Stephens , C. E. ; Boykin , D. W. Palladium-catalyzed N-arylation of O-methylamidoximes . Tetrahedron Lett. 2002 , 43 , 4221 – 4224 .
   Google Scholar
• Yin , J. ; Buchwald , S. L. Palladium-catalyzed intermolecular coupling of aryl halides and amides . Org. Lett. 2000 , 2 , 1101 – 1104 .
   Google Scholar
• Artamkina , G. A. ; Sergeev , A. G. ; Beletskaya , I. P. Palladium-catalyzed reaction of aryl halides with ureas . Tetrahedron Lett. 2001 , 42 , 4381 – 4384 .
   Google Scholar
• Sadighi , J. P. ; Harris , M. C. ; Buchwald , S. L. A highly active palladium catalyst system for the arylation of anilines. Tetrahedron Lett. 1998 , 39 , 5327 – 5330 .
   Google Scholar
• Huang , X. ; Anderson , K. W. ; Zim , D. ; Jiang , L. ; Klapars , A. ; Buchwald , S. L. Expanding Pd-catalyzed C-N bond-forming processes: The first amidation of arylsulfonates, aqueous amination, and complementarity with Cu-catalyzed reactions . J. Am. Chem. Soc. 2003 , 125 , 6653 – 6655 .
   PubMed Web of Science ®Google Scholar
• Begouin , A. ; Hesse , S. ; Queiroz , M.-J. R. P. ; Kirsch , G. Reactivity of substituted bromothiophenecarboxylates in palladium-catalyzed N-arylation of hetarylamines . Synthesis 2006 , 2794 – 2798 .
   Google Scholar
• Kuyper , L. F. ; Garvey , J. M. ; Baccanari , D. P. ; Champness , J. N. ; Stammers , D. K. ; Beddell , C. R. Pyrrolo[2,3-d]pyrimidines and pyrido[2,3-d]pyrimidines as conformationally restricted analogues of the antibacterial agent trimethoprim . Bioorg. Med. Chem. 1996 , 4 , 593 – 602 .
   Google Scholar
• Zhang , Y. ; Kawashima , K. ; Noguchi , M. A convenient synthesis of 2-functionalized pyrrolo[2,3-d]pyrido[1,2-a]pyrimidines . Heterocycles 2006 , 70 , 181 – 184 .
   Google Scholar