From paracetamol to rolipram and derivatives: Application of deacetylation-diazotation sequences and palladium-catalyzed matsuda-heck reaction

Synthesis (Germany)

Volumn 45, Issue 9, 2013, Pages 1174-1180

  Schmidt, Bernd ^a   Elizarov, Nelli ^a   Berger, René ^a   Petersen, Monibh ^a  

^a UNIVERSITY OF POTSDAM   (Germany)

Author keywords

acetanilides; deacetylation; diazonium salts; Matsuda Heck reaction; palladium

Indexed keywords

ACETANILIDES; AROMATIC CORES; CONJUGATE ADDITION; DEACETYLATION; DIAZONIUM SALTS; MATSUDA-HECK REACTION; OXIDATIVE FUNCTIONALIZATION; PALLADIUM-CATALYZED;

CHEMISTRY; PALLADIUM; SPEECH SYNTHESIS;

ACETYLATION;

ACRYLIC ACID; DIAZONIUM COMPOUND; N METHYLROLIPRAM; NITROMETHANE; PALLADIUM; PARACETAMOL; ROLIPRAM; ROLIPRAM DERIVATIVE; TERT BUTYL ALCOHOL; UNCLASSIFIED DRUG; WATER;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CONJUGATION; CONTROLLED STUDY; CYCLIZATION; DEACETYLATION; DIAZOTATION; DRUG SYNTHESIS; HYDROGENATION; MATSUDA HECK REACTION;

EID: 84876684472     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0032-1316874     Document Type: Article

References (34)

1. Karppanen H., Paakkari P., Orma A.-L, Paakkari I. Agents Actions: 1979; 9 84
2. Day J. P., Lindsay B., Riddell T., Jiang Z., Allcock R. W., Abraham A., Sookup S., Christian F., Bogum J., Martin E. K., Rae R. L., Anthony D., Rosair G. M., Houslay D. M., Huston E., Baillie G. S., Klussmann E., Houslay M. D., Adams D. R. J. Med. Chem.: 2011; 54 3331
3. Ortiz J. L., Milara J., Lluch J., De Diego A., Sanz C., Cortijo J. Allergy: 2013; 68 64
4. Fehrholz M., Bersani I., Kramer B. W., Speer C. P., Kunzmann S. PLoS One: 2012; 7 11
5. Oliva A. A., Kang Y., Furones C., Alonso O. F., Bruno O., Dietrich W. D., Atkins C. M. J. Neurochem.: 2012; 123 1019
6. Itoh K., Kanemasa S. J. Am. Chem. Soc.: 2002; 124 13394
7. Palomo C., Landa A., Mielgo A., Oiarbide M., Puente Á, Vera S. Angew. Chem. Int. Ed.: 2007; 46 8431
8. Vakulya B., Varga S., Soós T. J. Org. Chem.: 2008; 73 3475
9. Oliveira A. R. M, Villar J. A. F. P, Simonelli F., Gariani R. A., Wosch C. L., Zarbin P. H. G. Tetrahedron Lett.: 2007; 48 1507
10. Wu B., Kuhen K., Ngoc Nguyen T., Ellis D., Anaclerio B., He X., Yang K., Karanewsky D., Yin H., Wolff K., Bieza K., Caldwell J., He Y. Bioorg. Med. Chem. Lett.: 2006; 16 3430
11. Yang X.-F, Ding C.-H, Li X.-H, Huang J.-Q, Hou X.-L, Dai L.-X, Wang P.-J. J. Org. Chem.: 2012; 77 8980
12. Morse H. N. Ber. Dtsch. Chem. Ges.: 1878; 11 232
13. Schmidt B., Berger R., Hölter F. Org. Biomol. Chem.: 2010; 8 1406
14. Schmidt B., Berger R., Hölter F., Böge N., Kreipl A. Int. Patent Appl. WO 2010/122105 A1: 2009;; Chem. Abstr. 2010, 1336884.
15. Schmidt B., Hoelter F. Int. Patent Appl. WO 2008055927: 2008;; Chem. Abstr. 2008, 590195.
16. Schmidt B., Hölter F., Berger R., Jessel S. Adv. Synth. Catal.: 2010; 352 2463
17. Schmidt B., Berger R., Kelling A., Schilde U. Chem. Eur. J.: 2011; 17 7032
18. Schmidt B., Hölter F., Kelling A., Schilde U. J. Org. Chem.: 2011; 76 3357
19. Schmidt B., Hölter F. Org. Biomol. Chem.: 2011; 9 4914
20. Schmidt B., Geißler D. Eur. J. Org. Chem.: 2011; 4814
21. Schmidt B., Elizarov N. Chem. Commun.: 2012; 48 4350
22. Bonin H., Fouquet E., Felpin F.-X. Adv. Synth. Catal.: 2011; 353 3063
23. Kikukawa K., Matsuda T. Chem. Lett.: 1977; 159
24. Roglans A., Pla-Quintana A., Moreno-Mañas M. Chem. Rev.: 2006; 106 4622
25. Taylor J. G., Moro A. V., Correia C. R. D. Eur. J. Org. Chem.: 2011; 1403
26. Felpin F.-X, Nassar-Hardy L., Le Callonnec F., Fouquet E. Tetrahedron: 2011; 67 2815
27. Severino E. A., Costenaro E. R., Garcia A. L. L, Correia C. R. D. Org. Lett.: 2003; 5 305
28. Felpin F.-X, Miqueu K., Sotiropoulos J.-M, Fouquet E., Ibarguren O., Laudien J. Chem. Eur. J.: 2010; 16 5191
29. Selvakumar K., Zapf A., Spannenberg A., Beller M. Chem. Eur. J.: 2002; 8 3901
30. Garcia A. L. L, Carpes M. J. S, de Oca A. C. B. M, dos Santos M. A. G, Santana C. C., Correia C. R. D. J. Org. Chem.: 2005; 70 1050
31. Kokil P. B., Patil S. D., Ravindranathan T., Nair P. M. Tetrahedron Lett.: 1979; 20 989
32. Felluga F., Gombac V., Pitacco G., Valentin E. Tetrahedron: Asymmetry: 2005; 16 1341
33. Felpin F.-X, Fouquet E. Chem. Eur. J.: 2010; 16 12440
34. Hoshiko T., Ishihara H., Shino M., Mori N. Chem. Pharm. Bull.: 1993; 41 633