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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 4
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Original Articles

Simultaneous C- and N-Alkylation of 2-Oxo-4,6-diaryl-1,2,3,4-tetrahydropyridine-3-carbonitrile Under Solid–Liquid Phase-Transfer Conditions

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Pages 540-550 | Received 25 Feb 2009, Published online: 03 Feb 2010

REFERENCES

  • (a) Josein , H. ; Ko , S.-B. ; Bom , D. ; Curran , D. P. A general synthetic approach to the (20S)-camptothecin family of antitumor agents by a regiocontrolled cascade radical cyclization of aryl Isonitriles . Chem. Eur. J. 1998 , 4 , 67 – 83 ; (b) Comins , D. L. ; Saha , J. K. Concise synthesis of mappicine ketone and (±)-mappicine . J. Org. Chem. 1996 , 61 , 9623 – 9624 ; (c) Comins , D. L. ; Nolan , J. M. A practical six-step synthesis of (S)-camptothecin . Org. Lett. 2001 , 3 , 4255 – 4257 .
  • (a) Villemin , D. ; Liao , L. One-pot three-step synthesis of cerpegin . Tetrahedron Lett. 1996 , 37 , 8733 – 8734 ; (b) Lazaar , J. ; Hoarau , C. ; Mongin , F. ; Trécourt , F. ; Godard , A. ; Quéguiner , G. ; Marsais , F. One-pot four-step synthesis of cerpegin . Tetrahedron Lett. 2005 , 46 , 3811 – 3813 .
  • Buck , J. ; Madeley , J. P. ; Pattenden , G. Lithiation of 4-methoxy-2-pyridones: Synthetic entry to tenellin and funiculosin, and related natural 3,5-disubstituted 4-oxy-2-pyridones . J. Chem. Soc., Perkin Trans. 1 1992 , 1 , 67 – 77 .
  • (a) Dolle , R. E. ; Nicolaou , K. C. Total synthesis of elfamycins: Aurodox and efrotomycin, 2: Coupling of key intermediates and completion of the synthesis . J. Am. Chem. Soc. 1985 , 107 , 1695 – 1698 ; (b) Vogeley , L. ; Palm , G. J. ; Mesters , J. R. ; Hilgenfeld , R. Conformational change of elongation factor Tu (EF-Tu) induced by antibiotic binding . J. Biol. Chem. 2001 , 276 , 17149 – 17155 ; (c) Parreira , R. L. T. ; Abrahao , O. ; Galembeck , S. E. Conformational preferences of non-nucleoside HIV-1 reverse transcriptase inhibitors . Tetrahedron 2001 , 57 , 3243 – 3253 .
  • Sorbera , L. A. ; Castaner , J. Laquinimod. Drugs Future 2003, 28, 1059.
  • Li , Q. ; Mitscher , L. A. ; Shen , L. L. The 2-pyridone antibacterial agents: Bacterial topoisomerase inhibitors . Med. Res. Rev. 2000 , 20 , 231 .
  • (a) Dias , N. ; Vezin , H. ; Lansiaux , H. ; Lansiaux , A. ; Bailly , C. Topoisomerase inhibitors of marine origin and their potential use as anticancer agents . Top. Curr. Chem. 2005 , 253 , 89 ; (b) Doll , R. J. ; Kirschmeier , P. ; Bishop , W. R. Farnesyltransferase inhibitors as anticancer agents: Critical crossroads . Curr. Opin. Drug. Disc. Dev. 2004 , 7 , 478 .
  • Torres , M. ; Gil , S. ; Parra , M. New synthetic methods to 2-pyridone rings . Curr. Org. Chem. 2005 , 9 , 1757 – 1779 .
  • (a) Desai , N. D. ; Shah , R. D. Improved protocol for thorpe reaction: Synthesis of 4-amino-1-arylpyrazole using solid–liqiud phase-transfer conditions . Synth. Commun. 2008 , 38 , 309 – 315 ; (b) Desai , N. D. ; Shah , R. D. Improved synthesis and efficient chemoselective reduction of fused tetrazoles under phase-transfer conditions . Synthesis 2006 , 3275 – 3279 .
  • (a) Hopkins , G. ; Jonak , J. P. ; Minnemeyer , H. J. ; Tieckelmann , H. Alkylations of heterocyclic ambident anions II: Alkylation of 2-pyridone salts . J. Org. Chem. 1967 , 32 , 4040 – 4044 ; (b) Gallo , R. J. ; Makosza , M. ; Dou , H. J. M. ; Hassanaly , P. Applications of phase-transfer catalysis in heterocyclic chemistry . Adv. Heterocycl. Chem. 1984 , 36 , 175 – 234 ; (c) Dou , H. J. M. ; Hassanaly , P. ; Metzger , J. Alkylation d'anions ambidents en catalyse par transfert de phase: Cas des hydroxypyridines . J. Heterocycl. Chem. 1977 , 14 , 321 – 323 ; (d) Comins , D. ; Jianhua , G. N- vs. O-Alkylation in the mitsunobu reaction of 2-pyridone . Tetrahedron Lett. 1994 , 35 , 2819 – 2822 ; (e) Rico , I. ; Halvorsen , K. ; Dubrule , C. ; Lattes , A. Effect of micelles on cyclization reactions: The use of N-hexadecyl-2-chloropyridinium iodide as an amphiphilic carboxyl-activating agent in lactonization and lactamization . J. Org. Chem. 1994 , 59 , 415 – 420 ; (f) Liu , H. ; Ko , S. B. ; Josien , H. ; Curran , D. P. Selective N-functionalization of 6-substituted-2-pyridones . Tetrahedron Lett. 1995 , 36 , 8917 – 8920 ; (g) Koppe , T. ; Mederski , R. K. W. ; Osswald , M. ; Schwarz , M. On the regiochemistry of the alkylation of tert-butyl N-[6-butyl-1,2-dihydro-2-oxo-3-pyridylmethyl]carbamate: Precursor of a series of potent angiotensin II receptor antagonists . Tetrahedron Lett. 1995 , 36 , 377 – 380 ; (h) Almena , I. ; Diaz-Ortiz , A. ; Diez-Barra , E. ; de la Hoz , A. ; Loupy , A. Solvent-free benzylations of 2-pyridone: Regiospecific N- or C-alkylation . Chem. Lett. 1996 , 5 , 333 – 334 ; (i) Sato , T. ; Yoshimatsu , K. ; Otera , J. CsF in organic synthesis: Tuning of N- or O-alkylation of 2-pyridone . Synlett. 1995 , 845 – 846 ; (j) Bowman , W. R. ; Bridge , C. F. Regioselective synthesis of N-alkyl pyridones . Synth. Commun. 1999 , 29 , 4051 – 4059 ; (k) Nadin , A. ; Harrison , T. Synthesis of tricyclic pyridones by radical cyclization . Tetrahedron Lett. 1999 , 40 , 4073 – 4076 ; (l) Sugahara , M. ; Moritani , Y. ; Kuroda , T. ; Kondo , K. ; Shimadzu , H. ; Ukita , T. An efficient synthesis of the anti-asthmatic agent T-440: A selective N-alkylation of 2-pyridone . Chem. Pharm. Bull. 2000 , 48 , 589 – 591 ; (m) Janin , Y. L. ; Huel , C. ; Flad , G. ; Thirot , S. Methyl orthocarboxylates as methylating agents of heterocycles . Eur. J. Org. Chem. 2002 , 1763 – 1769 ; (n) Ruda , M. C. ; Bergman , J. ; Wu , J. Preparation of N-alkylated pyridones via selective N-alkylation of 2-alkoxypyridines on solid phase . J. Comb. Chem. 2002 , 4 , 530 – 535 ; (o) Olaf , R. L. ; Chris , M. Synthesis of carbocyclic pyrimidine nucleosides using the Mitsunobu reaction, part II: Influence of the solvent on N1- versus O2-alkylation . Synlett. 2006 , 324 – 326 .
  • (a) Bomika , Z. A. ; Andaburskaya , M. B. ; Pelcher , Y. É. ; Dubur , G. Y. 2-Oxopyridine derivatives . Khim. Geterotsikl. Soedin 1975 , 8 , 1108 – 1111 ; (b) Kuthan , J. ; Nesvadba , P. ; Donnerova , Z. ; Trska , P. Contribution to the study of cyclocondensations of cyanoacetic acid derivatives with benzylideneacetophenone . Coll. Czech. Chem. Commun. 1977 , 42 , 2152 – 2160 .
  • (a) Crystallographic Data Centre as supplementary publication numbers CCDC 183036: copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44-1223-336033 or e-mail: [email protected]): Patel , U. H. ; Dave , C. G. ; Jotani , M. M. ; Shah , H. C. 1,3-Dimethyl-2-oxo-4,6-diphenyl-1,2,3,4-tetrahydropyridine-3-carbonitrile. Acta Cryst. 2002, C58, o191; (b) CCDC 294954: Patel , U. H. ; Jotani , M. M. ; Shah , H. C. Crystal and molecular structure of 1,3-diethyl-2-oxo-4,6-diphenyl-1,2,3,4-tetrahydropyridine-3-carbonitrile. Anal. Sci. 2006, 22, 109; (c) CCDC 187605: Patel , U. H. ; Dave , C. G. ; Jotani , M. M. ; Shah , H. C. Crystal structure of 1,3-dibenzyl-2-oxo-4,6-diphenyl-1,2,3,4-tetrahydropyridine-3-carbonitrile, C32H26N2O. Z. Kristallogr.-New Cryst. Struct. 2002, 217, 29.
  • Miller , J. A. ; Dankwardt , J. W. Nickel-catalyzed cross-coupling of modified alkyl and alkenyl Grignard reagents with aryl- and heteroaryl nitriles: Activation of the C‒CN bond . Tetrahedron Lett. 2003 , 44 , 1907 – 1910 .
  • Dedicated to the memory of Dr. Chaitanya G. Dave.

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