An Expedient, Flexible and Convergent Access to Selectively Protected 1,5-Dicarbonyl Compounds. Applications to the Synthesis of 2,6-Disubstituted Pyridines and Thiopyridines

Jean Boivin; Floriane Carpentier; Rafik Jrad

doi:10.1055/s-2006-926464

PAPER

An Expedient, Flexible and Convergent Access to Selectively Protected 1,5-Dicarbonyl Compounds. Applications to the Synthesis of 2,6-Disubstituted Pyridines and Thiopyridines

Jean Boivin*, Floriane Carpentier, Rafik Jrad
Institut de Chimie des Substances Naturelles, Gif-sur-Yvette 91198, France
Fax: +33(1)69077247; e-Mail: jean.boivin@icsn.cnrs-gif.fr;

Abstract

Alle Artikel dieser Rubrik

Abstract

Intermolecular addition of 2-oxoalkyl radicals generated from the corresponding S-alkyl-O-ethyl dithiocarbonates on vinyl ketals afforded selectively protected 1,5-dicarbonyl compounds in good yields. These key-intermediates can be converted into a plethora of useful substances. Transformations to pyridines and thiopyridines were given as examples.

Key words

ketals - alkenes - ketones - pyridines - radical reactions

Volltext

Referenzen

References

1a Barton DHR. In Half a Century of Free Radical Chemistry Cambridge University Press; Cambridge: 1993.

1b Barton DHR. McCombie SW. J. Chem. Soc., Perkin Trans. 1 1975, 1574

1c Barton DHR. Ferreira JA. Jaszberenyi JC. In Preparative Carbohydrate Chemistry Hanessian S. Marcel Dekker; New York: 1997. p.151-172

1d Hong FT. Paquette LA. Chemtracts: Org. Chem. 1998, 11: 67

2a Zard SZ. Angew. Chem., Int. Ed. Engl. 1997, 36: 673

2b Zard SZ. In Radicals in Organic Synthesis Vol. 1: Renaud P. Sibi MP. Wiley-VCH; Weinheim: 2001. p.90-108

2c Quiclet-Sire B. Zard SZ. Pure Appl. Chem. 1997, 69: 645

2d Crich D. Quintero L. Chem. Rev. 1989, 89: 1413

3a Liard A. Quiclet-Sire B. Zard SZ. Tetrahedron Lett. 1996, 37: 5877

3b Quiclet-Sire B. Zard SZ. Tetrahedron Lett. 1998, 39: 9435

4 Boivin J. Jrad R. Juge S. Nguyen VT. Org. Lett. 2003, 5: 1645 ; and references cited therein

See, for example:

5a Saucy G. Koch W. Müller M. Fürst A. Helv. Chem. Acta 1970, 53: 964

5b Serini A. Logemann W. Hildebrand W. Chem. Ber. 1968, 72: 391

5c Santiago A. Montes de Lopez-Cepero I. Larson GL. Synth. Commun. 1986, 16: 697

5d Stork G. Borch R. J. Am. Chem. Soc. 1964, 86: 935

5e Hajos Z. Micheli R. Parrish D. Oliveto E. J. Org. Chem. 1967, 32: 3008

5f Green MJ. Abraham NA. Fleischer EB. Case J. Fried J. J. Chem. Soc., Chem. Commun. 1970, 234

See, for example:

6a Scott JW. Banner BL. Saucy G. J. Org. Chem. 1972, 37: 1664

6b Mitra RB. Reddy B. Synthesis 1989, 694

6c Cooke MP. J. Org. Chem. 1973, 38: 4082

6d Ballini R. Bartoli G. Synthesis 1993, 965

See, for example:

7a Jung ME. Tetrahedron 1976, 32: 3

7b McMurry JE. Rees KL. J. Org.Chem. 1978, 43: 3255

7c McMurry JE. Fleming MP. J. Am. Chem. Soc. 1974, 96: 4708

7d McMurry JE. Fleming MP. J. Org. Chem. 1976, 41: 896

7e Rapson WS. Robinson R. J. Chem. Soc. 1935, 1285

7f Nazarov IN. Zav’yalov SI. Izvest. Akad. Nauk SSSR, Otd. Khim. Nauk. 1952, 300 ; Chem. Abstr. 1953, 47, 5364

7g Ramachandran S. Newman MS. Org. Synth., Coll. Vol. 5 Wiley; New York: 1973. p.486

7h Hajos ZG. Parrish DR. J. Org. Chem. 1974, 39: 1612

7i Stork G. Loewenthal HJE. Mukharji PC. J. Am. Chem. Soc. 1956, 78: 501

7j Brown HC. Racherla US. Singh SM. Synthesis 1984, 922

7k Negishi EI. Luo FT. J. Org. Chem. 1983, 48: 2427

8a Seoane C. Soto JL. Quintéro M. Heterocycles 1980, 14: 337

8b Husson HP. Royer J. Chem. Soc. Rev. 1999, 28: 383

9a Durkopf E. Ber. Dtsch. Chem. Ges. 1887, 20: 444

9b Tschitschibabin AE. J. Prakt. Chem. 1924, 107: 122

9c Frank RL. Blegen JR. Dearborn RJ. Myers RL. Woodward FE. J. Am. Chem. Soc. 1946, 68: 1368

9d Weiss M. J. Am. Chem. Soc. 1952, 74: 200

9e Knoevenagel E. Justus Liebigs Ann. Chem. 1894, 281: 25

9f Rehberg RW. Kröhnke F. Justus Liebigs Ann. Chem. 1968, 717: 91

10 Varela JA. Saá C. Chem. Rev. 2003, 103: 3787

11a Pchelintseva NV. Chalaya SN. Kharchenko VG. Zh. Org. Khim. 1990, 26: 1904 ; Chem. Abstr. 1991, 115, 71334

11b Owton WM. Gallagher PT. Brunavs M. Synth. Commun. 1992, 22: 351

Among the plethoric literature data one can see:

12a Jones G. Pyridines and their Benzo Derivatives, In Comprehensive Heterocyclic Chemistry II Vol. 5: Katritzky A. Rees CW. Scriven EFV. Pergamon; Oxford: 1996. p.167-243

12b Smith DM. Pyridines, In Comprehensive Organic Chemistry Vol. 4: Barton DHR. Ollis D. Pergamon Press; Oxford: 1979. p.3-84

12c Kröhnke F. Synthesis 1976, 1

12d Elderfield RC. Heterocyclic Compounds Wiley; New York: 1950. p.455-472

13 Boivin J. Pothier J. Zard SZ. Tetrahedron Lett. 1999, 40: 3701

14 Tate EW. Zard SZ. Tetrahedron Lett. 2002, 43: 4683

15a Kloosterziel H. Backer HJ. Recl. Trav. Chim. Pays-Bas 1952, 71: 361

15b Patel BA. Kim JI. Bender DD. Kao LC. Heck R. J. Org. Chem. 1981, 46: 1061

15c Gutzmann J. Messinger P. Arch. Pharm. (Weinheim Ger.) 1995, 328: 523

16 Friedel C. Crafts JM. C. R. Acad. Sci. 1877, 84: 1392

17 Huet F. Lechevallier A. Pellet M. Synthesis 1978, 63

18 McElvain SM. Goese MA. J. Am. Chem. Soc. 1943, 65: 2227

19 Talik T. Talik S. Ban-Oganowska H. Synthesis 1974, 293

20a Blank B. DiTullio NW. Miao C. Owings FF. Gleason JG. Ross ST. Berkoff CE. Saunders HL. J. Med. Chem. 1974, 10: 1064

20b Sucharda E. Troszkiewiczowna CZ. Rocz. Chem. 1932, 12: 493 ; Chem. Abstr. 1933, 27, 5076

20c Newman MB. Karnes HA. J. Org. Chem. 1966, 31: 3980

See, for example:

21a Quiclet-Sire B. Quintero L. Sanchez-Jimenez G. Zard SZ. Synlett 2002, 75

21b Lopez-Ruiz H. Zard SZ. Chem. Commun. 2001, 2618

21c Boutillier P. Zard SZ. Chem. Commun. 2001, 1304

21d Quiclet-Sire B. Wendeborn (née Bertrand) F. Zard SZ. Chem. Commun. 2002, 2214

21e Lusinchi M. Stanbury TV. Zard SZ. Chem. Commun. 2002, 1532

22a Forbes JE. Tailhan C. Zard SZ. Tetrahedron Lett. 1990, 31: 2565

22b Boivin J. Yousfi M. Zard SZ. Tetrahedron Lett. 1994, 35: 9553

22c Axon J. Boiteau L. Boivin J. Forbes JE. Zard SZ. Tetrahedron Lett. 1994, 35: 1719

22d Liard A. Quiclet-Sire B. Saicic RN. Zard SZ. Tetrahedron Lett. 1997, 38: 1759

22e Ly TM. Quiclet-Sire B. Sortais B. Zard SZ. Tetrahedron Lett. 1999, 40: 2533

22f Udding JH. Hiemstra H. Speckamp WN. J. Org. Chem. 1994, 59: 3721

22g Udding JH. Giesselink JPM. Hiemstra H. Speckamp WN. J. Org. Chem. 1994, 59: 6671

23a Brown MD. Gillon DW. Meakins GD. Whitham GH. J. Chem. Soc., Perkin Trans. 1 1985, 1623

23b Cholleton N. Zard SZ. Tetrahedron Lett. 1998, 40: 7295

24a Doelling W. Vogt A. Augustin M. Monatsh. Chem. 1989, 120: 879

24b Parham WE. Harper ET. Berger RS. J. Am. Chem. Soc. 1960, 82: 4932