'Reductive Heck reaction' of 6-halopurines

Tetrahedron Letters

Volumn 45, Issue 2, 2004, Pages 273-276

  Tobrman, Tomáš ^a   Dvořák, Dalimil ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

Alkylpurine; Heck reaction; Pd catalysis

Indexed keywords

ALKENE; PURINE DERIVATIVE;

ALKYLATION; ANIMAL CELL; ARTICLE; CHEMICAL BOND; CONTROLLED STUDY; HECK REACTION; HUMAN; HUMAN CELL; MICHAEL ADDITION; NONHUMAN; RACEMIC MIXTURE; STEREOCHEMISTRY;

EID: 0346996545     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.181     Document Type: Article

References (33)

1. For recent reviews, see: Söderberg B.C. Abel E.W., Stone F.G.A., Wilkinson G. Comprehensive Organometallic Chemistry II. Vol. 12:1995;241-297 Pergamon, Oxford, UK, Overman L.E. Pure Appl. Chem. 66:1994;1423-1430 deMeijere E., Meyer F.E. Angew. Chem., Int. Ed. Engl. 33:1994;2379-2411 Cabri W., Candiani I. Acc. Chem. Res. 28:1995;2-7.
2. For recent reviews, see: Söderberg B.C. Abel E.W., Stone F.G.A., Wilkinson G. Comprehensive Organometallic Chemistry II. Vol. 12:1995;241-297 Pergamon, Oxford, UK, Overman L.E. Pure Appl. Chem. 66:1994;1423-1430 deMeijere E., Meyer F.E. Angew. Chem., Int. Ed. Engl. 33:1994;2379-2411 Cabri W., Candiani I. Acc. Chem. Res. 28:1995;2-7.
3. For recent reviews, see: Söderberg B.C. Abel E.W., Stone F.G.A., Wilkinson G. Comprehensive Organometallic Chemistry II. Vol. 12:1995;241-297 Pergamon, Oxford, UK, Overman L.E. Pure Appl. Chem. 66:1994;1423-1430 deMeijere E., Meyer F.E. Angew. Chem., Int. Ed. Engl. 33:1994;2379-2411 Cabri W., Candiani I. Acc. Chem. Res. 28:1995;2-7.
4. For recent reviews, see: Söderberg B.C. Abel E.W., Stone F.G.A., Wilkinson G. Comprehensive Organometallic Chemistry II. Vol. 12:1995;241-297 Pergamon, Oxford, UK, Overman L.E. Pure Appl. Chem. 66:1994;1423-1430 deMeijere E., Meyer F.E. Angew. Chem., Int. Ed. Engl. 33:1994;2379-2411 Cabri W., Candiani I. Acc. Chem. Res. 28:1995;2-7.
5. For examples, see: Li J.J., Gribble G.W. Palladium in Heterocyclic Chemistry. Baldwin J.E., Williams R.M. Tetrahedron Organic Chemistry Series. 2000;Pergamon, Oxford, UK.
6. Bräthe A., Gundersen L.-L., Rise F., Eriksen A.B., Vollsnes A.V., Wang L. Tetrahedron. 55:1999;211-228.
7. Bakkestuen A.K., Gundersen L.-L., Langli G., Liu F., Nölsoe J.M.J. Bioorg. Med. Chem. Lett. 10:2000;1207-1210.
8. Bräthe A., Andersen G., Gundersen L.-L., Malterud K.E., Rise F. Bioorg. Med. Chem. 10:2002;1581-1586.
9. Jacobson K.A., Shi D., Gallo-Rodriguez C., Manning M., Müller C., Daly J.W., Meumayer J.L., Kiriasis L., Pfleiderer W. J. Med. Chem. 36:1993;2639-2644.
10. Havelková M., Studenovský M., Dvořák D. Collect. Czech. Chem. Commun. 65:2000;797-804.
11. Gundersen L.-L. Tetrahedron Lett. 35:1994;3155-3158 Gundersen L.-L., Bakkestuen A.K., Aasen A.J., Øverås, Rise F. Tetrahedron. 50:1994;9743-9756 Havelková M., Hocek M., Česnek M., Dvořák D. Synlett. 1999;1145-1147 Havelková M., Dvořák D., Hocek M. Synthesis. 2001;1704-1710. For a recent review on Pd and other transition metal mediated syntheses of purine derivatives, see: Hocek M. Eur. J. Org. Chem. 23:2003;245-254. For a recent review on Pd-catalyzed syntheses of nucleosides, see: Agrofoglio L.A., Gillaizeau I., Saito Y. Chem. Rev. 103:2003;1875-1916.
12. Gundersen L.-L. Tetrahedron Lett. 35:1994;3155-3158 Gundersen L.-L., Bakkestuen A.K., Aasen A.J., Øverås, Rise F. Tetrahedron. 50:1994;9743-9756 Havelková M., Hocek M., Česnek M., Dvořák D. Synlett. 1999;1145-1147 Havelková M., Dvořák D., Hocek M. Synthesis. 2001;1704-1710. For a recent review on Pd and other transition metal mediated syntheses of purine derivatives, see: Hocek M. Eur. J. Org. Chem. 23:2003;245-254. For a recent review on Pd-catalyzed syntheses of nucleosides, see: Agrofoglio L.A., Gillaizeau I., Saito Y. Chem. Rev. 103:2003;1875-1916.
13. Gundersen L.-L. Tetrahedron Lett. 35:1994;3155-3158 Gundersen L.-L., Bakkestuen A.K., Aasen A.J., Øverås, Rise F. Tetrahedron. 50:1994;9743-9756 Havelková M., Hocek M., Česnek M., Dvořák D. Synlett. 1999;1145-1147 Havelková M., Dvořák D., Hocek M. Synthesis. 2001;1704-1710. For a recent review on Pd and other transition metal mediated syntheses of purine derivatives, see: Hocek M. Eur. J. Org. Chem. 23:2003;245-254. For a recent review on Pd-catalyzed syntheses of nucleosides, see: Agrofoglio L.A., Gillaizeau I., Saito Y. Chem. Rev. 103:2003;1875-1916.
14. Gundersen L.-L. Tetrahedron Lett. 35:1994;3155-3158 Gundersen L.-L., Bakkestuen A.K., Aasen A.J., Øverås, Rise F. Tetrahedron. 50:1994;9743-9756 Havelková M., Hocek M., Česnek M., Dvořák D. Synlett. 1999;1145-1147 Havelková M., Dvořák D., Hocek M. Synthesis. 2001;1704-1710. For a recent review on Pd and other transition metal mediated syntheses of purine derivatives, see: Hocek M. Eur. J. Org. Chem. 23:2003;245-254. For a recent review on Pd-catalyzed syntheses of nucleosides, see: Agrofoglio L.A., Gillaizeau I., Saito Y. Chem. Rev. 103:2003;1875-1916.
15. Gundersen L.-L. Tetrahedron Lett. 35:1994;3155-3158 Gundersen L.-L., Bakkestuen A.K., Aasen A.J., Øverås, Rise F. Tetrahedron. 50:1994;9743-9756 Havelková M., Hocek M., Česnek M., Dvořák D. Synlett. 1999;1145-1147 Havelková M., Dvořák D., Hocek M. Synthesis. 2001;1704-1710. For a recent review on Pd and other transition metal mediated syntheses of purine derivatives, see: Hocek M. Eur. J. Org. Chem. 23:2003;245-254. For a recent review on Pd-catalyzed syntheses of nucleosides, see: Agrofoglio L.A., Gillaizeau I., Saito Y. Chem. Rev. 103:2003;1875-1916.
16. Gundersen L.-L. Tetrahedron Lett. 35:1994;3155-3158 Gundersen L.-L., Bakkestuen A.K., Aasen A.J., Øverås, Rise F. Tetrahedron. 50:1994;9743-9756 Havelková M., Hocek M., Česnek M., Dvořák D. Synlett. 1999;1145-1147 Havelková M., Dvořák D., Hocek M. Synthesis. 2001;1704-1710. For a recent review on Pd and other transition metal mediated syntheses of purine derivatives, see: Hocek M. Eur. J. Org. Chem. 23:2003;245-254. For a recent review on Pd-catalyzed syntheses of nucleosides, see: Agrofoglio L.A., Gillaizeau I., Saito Y. Chem. Rev. 103:2003;1875-1916.
17. Bozell J.J., Vogt C.E., Gozum J. J. Org. Chem. 56:1991;2584-2587 Schnyder A., Aemmer T., Indolese A.F., Pittelkow U., Studer M. Adv. Synth. Catal. 344:2002;495-498.
18. Bozell J.J., Vogt C.E., Gozum J. J. Org. Chem. 56:1991;2584-2587 Schnyder A., Aemmer T., Indolese A.F., Pittelkow U., Studer M. Adv. Synth. Catal. 344:2002;495-498.
19. For examples, see: Nakatsu K., Kinoshita K., Kanda H., Isobe K., Nakamura Y., Kawaguchi S. Chem. Lett. 23:1980;913-914 Isobe K., Kawaguchi S. Heterocycles. 16:1981;1603-1612 Yamamoto Y., Yanagi A. Chem. Pharm. Bull. 30:1982;2003-2010 Mantovani A., Crociani B. J. Organomet. Chem. 236: 1982;C37-C40 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 251:1983;393-441 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 291:1985;259-271 Bertani R., Berton A., Di Bianca F., Crociani B. J. Organomet. Chem. 303:1986;283-299 Urata H., Tanaka M., Fuchikami T. Chem. Lett. 23:1987;751-754 Benneche T. Acta Chem. Scand. 44:1990;927-931.
20. For examples, see: Nakatsu K., Kinoshita K., Kanda H., Isobe K., Nakamura Y., Kawaguchi S. Chem. Lett. 23:1980;913-914 Isobe K., Kawaguchi S. Heterocycles. 16:1981;1603-1612 Yamamoto Y., Yanagi A. Chem. Pharm. Bull. 30:1982;2003-2010 Mantovani A., Crociani B. J. Organomet. Chem. 236: 1982;C37-C40 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 251:1983;393-441 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 291:1985;259-271 Bertani R., Berton A., Di Bianca F., Crociani B. J. Organomet. Chem. 303:1986;283-299 Urata H., Tanaka M., Fuchikami T. Chem. Lett. 23:1987;751-754 Benneche T. Acta Chem. Scand. 44:1990;927-931.
21. For examples, see: Nakatsu K., Kinoshita K., Kanda H., Isobe K., Nakamura Y., Kawaguchi S. Chem. Lett. 23:1980;913-914 Isobe K., Kawaguchi S. Heterocycles. 16:1981;1603-1612 Yamamoto Y., Yanagi A. Chem. Pharm. Bull. 30:1982;2003-2010 Mantovani A., Crociani B. J. Organomet. Chem. 236: 1982;C37-C40 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 251:1983;393-441 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 291:1985;259-271 Bertani R., Berton A., Di Bianca F., Crociani B. J. Organomet. Chem. 303:1986;283-299 Urata H., Tanaka M., Fuchikami T. Chem. Lett. 23:1987;751-754 Benneche T. Acta Chem. Scand. 44:1990;927-931.
22. For examples, see: Nakatsu K., Kinoshita K., Kanda H., Isobe K., Nakamura Y., Kawaguchi S. Chem. Lett. 23:1980;913-914 Isobe K., Kawaguchi S. Heterocycles. 16:1981;1603-1612 Yamamoto Y., Yanagi A. Chem. Pharm. Bull. 30:1982;2003-2010 Mantovani A., Crociani B. J. Organomet. Chem. 236: 1982;C37-C40 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 251:1983;393-441 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 291:1985;259-271 Bertani R., Berton A., Di Bianca F., Crociani B. J. Organomet. Chem. 303:1986;283-299 Urata H., Tanaka M., Fuchikami T. Chem. Lett. 23:1987;751-754 Benneche T. Acta Chem. Scand. 44:1990;927-931.
23. For examples, see: Nakatsu K., Kinoshita K., Kanda H., Isobe K., Nakamura Y., Kawaguchi S. Chem. Lett. 23:1980;913-914 Isobe K., Kawaguchi S. Heterocycles. 16:1981;1603-1612 Yamamoto Y., Yanagi A. Chem. Pharm. Bull. 30:1982;2003-2010 Mantovani A., Crociani B. J. Organomet. Chem. 236: 1982;C37-C40 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 251:1983;393-441 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 291:1985;259-271 Bertani R., Berton A., Di Bianca F., Crociani B. J. Organomet. Chem. 303:1986;283-299 Urata H., Tanaka M., Fuchikami T. Chem. Lett. 23:1987;751-754 Benneche T. Acta Chem. Scand. 44:1990;927-931.
24. For examples, see: Nakatsu K., Kinoshita K., Kanda H., Isobe K., Nakamura Y., Kawaguchi S. Chem. Lett. 23:1980;913-914 Isobe K., Kawaguchi S. Heterocycles. 16:1981;1603-1612 Yamamoto Y., Yanagi A. Chem. Pharm. Bull. 30:1982;2003-2010 Mantovani A., Crociani B. J. Organomet. Chem. 236: 1982;C37-C40 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 251:1983;393-441 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 291:1985;259-271 Bertani R., Berton A., Di Bianca F., Crociani B. J. Organomet. Chem. 303:1986;283-299 Urata H., Tanaka M., Fuchikami T. Chem. Lett. 23:1987;751-754 Benneche T. Acta Chem. Scand. 44:1990;927-931.
25. For examples, see: Nakatsu K., Kinoshita K., Kanda H., Isobe K., Nakamura Y., Kawaguchi S. Chem. Lett. 23:1980;913-914 Isobe K., Kawaguchi S. Heterocycles. 16:1981;1603-1612 Yamamoto Y., Yanagi A. Chem. Pharm. Bull. 30:1982;2003-2010 Mantovani A., Crociani B. J. Organomet. Chem. 236: 1982;C37-C40 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 251:1983;393-441 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 291:1985;259-271 Bertani R., Berton A., Di Bianca F., Crociani B. J. Organomet. Chem. 303:1986;283-299 Urata H., Tanaka M., Fuchikami T. Chem. Lett. 23:1987;751-754 Benneche T. Acta Chem. Scand. 44:1990;927-931.
26. For examples, see: Nakatsu K., Kinoshita K., Kanda H., Isobe K., Nakamura Y., Kawaguchi S. Chem. Lett. 23:1980;913-914 Isobe K., Kawaguchi S. Heterocycles. 16:1981;1603-1612 Yamamoto Y., Yanagi A. Chem. Pharm. Bull. 30:1982;2003-2010 Mantovani A., Crociani B. J. Organomet. Chem. 236: 1982;C37-C40 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 251:1983;393-441 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 291:1985;259-271 Bertani R., Berton A., Di Bianca F., Crociani B. J. Organomet. Chem. 303:1986;283-299 Urata H., Tanaka M., Fuchikami T. Chem. Lett. 23:1987;751-754 Benneche T. Acta Chem. Scand. 44:1990;927-931.
27. For examples, see: Nakatsu K., Kinoshita K., Kanda H., Isobe K., Nakamura Y., Kawaguchi S. Chem. Lett. 23:1980;913-914 Isobe K., Kawaguchi S. Heterocycles. 16:1981;1603-1612 Yamamoto Y., Yanagi A. Chem. Pharm. Bull. 30:1982;2003-2010 Mantovani A., Crociani B. J. Organomet. Chem. 236: 1982;C37-C40 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 251:1983;393-441 Crociani B., Di Bianca F., Giovenco A., Scrivanti A. J. Organomet. Chem. 291:1985;259-271 Bertani R., Berton A., Di Bianca F., Crociani B. J. Organomet. Chem. 303:1986;283-299 Urata H., Tanaka M., Fuchikami T. Chem. Lett. 23:1987;751-754 Benneche T. Acta Chem. Scand. 44:1990;927-931.
28. Gundersen L.-L. Acta Chem. Scand. 50:1996;462-465.
29. Similar chelates were found to be responsible for the failure of the carbonylation of aliphatic amines: Hegedus L.S., McKearin J.M. J. Am. Chem. Soc. 104:1982;2444-2451.
30. With phenyltributyltin, the product of Stille coupling (9-benzyl-6-phenylpurine) was formed, while no reaction took place with phenylboronic acid.
31. 2 338.1743, found 338.1735.
32. Formation of the ethyl derivative 8 remains unclear. Acetoxy derivative 6g is not an intermediate, since it is stable under the conditions used. In our opinion, the most probable way for the formation of 8 involves formation of a 6-vinylpurine derivative by β-elimination of acetate from the product of insertion of vinyl acetate. The ethyl derivative is then formed by Pd-catalyzed transfer hydrogenation of the vinyl group.
33. 2H led to the formation of the product analogous to 3a , but the yield was very low (8%).