Regioselective Synthesis of 1,4,6-Trisubstituted-2-Pyridinones and 2,3-Disubstituted (2H)-Isoquinolin-1-ones via Tandem Stille Reaction/Heterocyclisation

Khalil Cherry; Alain Duchêne; Jérôme Thibonnet; Jean-Luc Parrain; Mohamed Abarbri

doi:10.1055/s-2005-870009

PAPER

Regioselective Synthesis of 1,4,6-Trisubstituted-2-Pyridinones and 2,3-Disubstituted (2H)-Isoquinolin-1-ones via Tandem Stille Reaction/Heterocyclisation

Khalil Cherry^a, Alain Duchêne^a, Jérôme Thibonnet^a,b, Jean-Luc Parrain^b, Mohamed Abarbri*^a
^a Laboratoire de Synthèse et Physicochimie Organique et Thérapeutique, Faculté des Sciences de Tours, Parc de Grandmont, EA 3857, 37200 Tours, France
Fax: +33(2)47367073; e-Mail: mohamed.abarbri@univ-tours.fr;
^b Laboratoire Symbio, Equipe Synthèse par Voie Organométallique, associé au CNRS (UMR 6178, Université Paul Cézanne, Aix Marseille III, Campus scientifique de Saint Jérôme, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France

Abstract

All articles of this category

Abstract

A general route to 1,4,6-trisubstituted 2-pyridinones and 2,3-disubstituted (2H)-isoquinolin-1-ones from (Z)-3-iodovinylic amides 1a-h and 2-iodo N-substituted benzamides 2a-f is described, including compounds bearing a substituent on the aromatic ring. Treatment of (Z)-β-iodovinylic amides 1a-h and 2-iodobenzamides 2a-f with various allenyltributyltin reagents in the presence of palladium acetate, triphenylphosphine and tetrabutylammonium bromide in acetonitrile provided good yields of the corresponding 1,4,6-trisubstituted 2-pyridinones 3a-k and 2,3-disubstituted (2H)-isoquinolin-1-ones 4a-i via tandem Stille reaction and 6-endo-dig azacyclisation.

Key words

pyridinones - isoquinolinones - tributylstannylallenes - palladium catalyst - azacyclisation

Full Text

References

For recent and various synthesis methods, see:

1a Hong P. Yamazaki H. Synthesis 1977, 50

1b Deodhar K. Kekare M. Pednekar S. Synthesis 1985, 328

1c Barluenga J. Tomãs M. Suãrez-Sobrino A. Gotor V. Tetrahedron Lett. 1988, 29: 4855

1d Chandra Sheker Reddy A. Narsaiah B. Venkataratnam R. Tetrahedron Lett. 1996, 37: 2829

1e Takaoka K. Aoyama T. Shioiri T. Tetrahedron Lett. 1996, 37: 4973

1f Katritzky A. Belyakov S. Sorochinsky A. Henderson S. Chen J. J. Org. Chem. 1997, 62: 6210

1g Furukawa I. Fujisawa H. Kawazome M. Nakai Y. Ohta T. Synthesis 1998, 1715

1h Ghosez L. Jnoff E. Bayard P. Sainte F. Beaudegnies R. Tetrahedron 1999, 55: 3387

1i Grosche P. Höltzel A. Walk T. Trautwein A. Jung G. Synthesis 1999, 1961

1j Zhang S. Liebeskind L. J. Org. Chem. 1999, 64: 4042

1k Alberola A. Calvo L. Ortega A. Carmen Sańudo Ruiz M. Yustos P. J. Org. Chem. 1999, 64: 9493

1l Brun E. Gil S. Mestres R. Parra M. Synthesis 2000, 273

1m Paulvannan K. Chen T. J. Org. Chem. 2000, 65: 6160

2a Flitsh W. Schindler SR. Synthesis 1975, 685

2b Rene B. Michele BC. Synthesis 1981, 729

2c Graham SP. J. Org. Chem. 1982, 47: 3787

2d Yasuhiro U. Naofumi K. Eiko M. Miwako M. Masakatsu S. J. Am. Chem. Soc. 1989, 11: 3725

2e Jacqueline EMK. Henk T. Regina L. Henk G. Adrian PI. J. Med. Chem. 1998, 41: 3987

2f Sashida H. Kawamukai A. Synthesis 1999, 1145

3a Smith D. In Comprehensive Organic Chemistry Vol. 4: Sammes PG. Pergamon; Oxford: 1979. p.3

3b McKillop A. Boulton A. In Comprehensive Heterocyclic Chemistry Vol. 2: McKillop A. Boulton A. Pergamon; Oxford: 1984. p.67

4a Schultz A. Chem. Rev. 1973, 73: 385

4b Kelly T. Bell S. Osashi N. Armstrong-Chong J. J. Am. Chem. Soc. 1988, 110: 6471

4c Curran D. Liu H. J. Am. Chem. Soc. 1992, 114: 5863

5 Cox R. O’hagan D. J. Chem. Soc., Perkin Trans. 1 1991, 2537

6 Williams D. Lowder P. Gu Y.-G. Tetrahedron Lett. 1997, 38: 327

7 Kozikowski A. Campiani G. Sun L.-Q. Wang S. Saxena A. Doctor B. J. Am. Chem. Soc. 1996, 118: 11357

8 Brickner S. Chem. Ind. (London) 1997, 131

9 Murray T. Zimmerman S. Tetrahedron Lett. 1995, 36: 7627

10 Margolin SB. inventors; US Patent 59214.

11 Jones G. In Comprehensive Heterocyclic Chemistry II Vol. 8: Katritzky A. Rees CW. Scriven EF. Pergamon; Oxford: 1996. p.395-510

12 Mohrle H. Weber H. Tetrahedron 1970, 26: 2953

13 Jones G. Org. React. 1967, 15: 204

14 Bailey TD. Goe GL. Scriven EFV. In Heterocyclic Compounds Vol. 14: Newkome GR. Wiley; New York: 1984. Part 5. p.1

15a Kappe T. Pocivalnik D. Heterocycles 1983, 20: 1367

15b Tutonda MG. Vandenberghe SM. Van Aken KJ. Hoornaert GJ. J. Org. Chem. 1992, 57: 2935

15c Sheehan SM. Padwa A. J. Org. Chem. 1997, 62: 438

16a Duchêne A. Abarbri M. Parrain J.-L. Kitamura M. Noyori R. Synlett 1994, 524

16b Abarbri M. Parrain J.-L. Cintrat JC. Duchêne A. Synthesis 1996, 82

17 Abarbri M. Parrain J.-L. Duchêne A. Synth. Commun. 1998, 28: 239

18 Cherry K. Thibonnet J. Duchêne A. Parrain J.-L. Abarbri M. Tetrahedron Lett. 2004, 45: 2063

19 Rousset S. Abarbri M. Thibonnet J. Duchêne A. Parrain J.-L. Org. Lett. 1999, 1: 701

20a Rousset S. Thibonnet J. Abarbri M. Duchêne A. Parrain J.-L. Synlett 2000, 260

20b Rousset S. Abarbri M. Thibonnet J. Duchêne A. Parrain J.-L. Chem. Commun. 2000, 1987

20c Rousset S. Abarbri M. Thibonnet J. Parrain J.-L. Duchêne A. Tetrahedron Lett. 2003, 44: 7633

21 Cherry K. Abarbri M. Parrain J.-L. Duchene A. Tetrahedron Lett. 2003, 44: 5791

22 Allenyltin reagents were prepared from 3-bromoprop-1-yne, magnesium and tributyltin chloride under lead(II) catalysis. Tanaka H. Abdul Hai A. Ogawa H. Torii S. Synlett 1993, 835

23a Pelletier SW. Chemistry of the Alkaloids Van Nostrand Reinhold Co; New York: 1970.

23b Shamma M. Moniot J. Isoquinoline Alkaloids Research Plenum Press; New York: 1978.

23c Ninomiya I. Naito T. The Alkaloids Vol. 22: Brossi AR. Academic Press; New York: 1983. p.189-279

24 Belgonkar VH. Usgaonkar RN. Tetrahedron Lett. 1975, 3849

25 Stanoeva E. Haimova M. Ognyanov V. Liebigs Ann. Chem. 1984, 389

26 Tirodkar RB. Usgaonkar RN. Indian J. Chem., Sect. B 1972, 10: 1060

27 Mali RS. Kulkani BK. Shankaran K. Synthesis 1982, 329

28 Kiselyov AS. Tetrahedron Lett. 1995, 36: 493

29 Lu W.-D. Lin C.-F. Wang C.-J. Wang S.-J. Wu M.-J. Tetrahedron 2002, 58: 7315

30a Stille JK. Angew. Chem., Int. Ed. Engl. 1986, 25: 508

30b Stille JK. Groh BL. J. Am. Chem. Soc. 1987, 109: 813

30c Mitchell TN. Synthesis 1992, 803

30d Farina V. In Comprehensive Organometallic Chemistry II Vol. 12: Abel EW. Stone FG. Wilkinson G. Elsevier; Oxford: 1995. p.161-241

30e Farina V. Roth GP. In Advances in Metal-Organic Chemistry Vol. 5: Liebeskind LS. JAI Press; New York: 1996. p.1-53

30f Farina V. Krishnamurthy V. Scott WJ. Org. React. 1997, 50: 1

30g Farina V. Krishnamurthy V. The Stille Reaction Wiley; New York: 1999.

31 Larock RC. He Y. Leon WW. Han X. Refvik MD. Zenner MJ. J. Org. Chem. 1998, 63: 2154

32a Meyers AI. Temple DL. Haidukewych D. Mihelich ED. J. Org. Chem. 1974, 39: 2787

32b Meyers AI. Mihelich ED. J. Org. Chem. 1975, 40: 3158

33 Ruda MC. Bergman J. Wu J. J. Comb. Chem. 2002, 4: 530

34 Ehm W. Liebigs Ann. Chem. 1977, 1642