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

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2005(14): 2349-2356
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

Further Information

Publication History

Received 21 February 2005
Publication Date:
13 July 2005 (online)

Abstract
Full Text
References

Permissions and Reprints 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

References

For recent and various synthesis methods, see:
1a Hong P. Yamazaki H. Synthesis 1977, 50

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

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

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

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

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

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

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

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

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

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

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

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

Crossref Google Scholar
2a Flitsh W. Schindler SR. Synthesis 1975, 685

Article in Thieme Connect Google Scholar
2b Rene B. Michele BC. Synthesis 1981, 729

Article in Thieme Connect Google Scholar
2c Graham SP. J. Org. Chem. 1982, 47: 3787

Article in Thieme Connect Google Scholar
2d Yasuhiro U. Naofumi K. Eiko M. Miwako M. Masakatsu S. J. Am. Chem. Soc. 1989, 11: 3725

Article in Thieme Connect Google Scholar
2e Jacqueline EMK. Henk T. Regina L. Henk G. Adrian PI. J. Med. Chem. 1998, 41: 3987

Article in Thieme Connect Google Scholar
2f Sashida H. Kawamukai A. Synthesis 1999, 1145

Article in Thieme Connect Google Scholar
3a Smith D. In Comprehensive Organic Chemistry Vol. 4: Sammes PG. Pergamon; Oxford: 1979. p.3

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

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

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

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

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

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

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

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

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

Crossref Google Scholar
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

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

Crossref Google Scholar
13 Jones G. Org. React. 1967, 15: 204

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

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

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

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

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

Article in Thieme Connect Google Scholar
16b Abarbri M. Parrain J.-L. Cintrat JC. Duchêne A. Synthesis 1996, 82

Article in Thieme Connect Google Scholar
17 Abarbri M. Parrain J.-L. Duchêne A. Synth. Commun. 1998, 28: 239

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

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

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

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

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

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

Crossref Google Scholar
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

Article in Thieme Connect Google Scholar
23a Pelletier SW. Chemistry of the Alkaloids Van Nostrand Reinhold Co; New York: 1970.

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

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

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

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

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

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

Article in Thieme Connect Google Scholar
28 Kiselyov AS. Tetrahedron Lett. 1995, 36: 493

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

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

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

Google Scholar
30c Mitchell TN. Synthesis 1992, 803

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

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

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

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

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

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

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

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

Crossref Google Scholar
34 Ehm W. Liebigs Ann. Chem. 1977, 1642

Google Scholar