Catechol reactivity: Synthesis of dopamine derivatives substituted at the 6-position

Synthetic Communications

Volumn 47, Issue 5, 2017, Pages 435-441

  Rote, Jennifer C ^a   Malkowski, Sarah N ^a   Cochrane, C Skyler ^a   Bailey, Gabrielle E ^a   Brown, Noah S ^a   Cafiero, Mauricio ^a   Peterson, Larryn W ^a  

^a RHODES COLLEGE   (United States)

Author keywords

Boron tribromide; catecholamine; dopamine; Hammett constant; O demethylation

Indexed keywords

6 BROMODOPAMINE; 6 CARBOXYDOPAMINE; 6 CYANODOPAMINE; ACETIC ACID; AMMONIA; AROMATIC COMPOUND; BORON TRIBROMIDE; BROMIDE; CATECHOL; CATECHOLAMINE DERIVATIVE; DOPAMINE DERIVATIVE; ETHER DERIVATIVE; FORMIC ACID; ISOQUINOLINE; NITROGEN; PARAFORMALDEHYDE; PHENOL; PROTON; TETRAHYDROISOQUINOLINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DEACETYLATION; DRUG SYNTHESIS; HYDROGEN BOND; HYDROPHILICITY; HYDROPHOBICITY; MASS SPECTROMETRY; PICTET SPENGLER CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

EID: 85010682955     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2016.1269350     Document Type: Article

References (27)

1. Sidharthan, N. P.,; Minchin, R. F.,; Butcher, N. J., J. Biol. Chem. 2013, 288, 34364–34374.
2. Loke, H.,; Harley, V.,; Lee, J., Int. J. Biochem. Cell Biol. 2015, 65, 139–150.
3. Mueller, T., Drugs 2015, 75, 157–174.
4. Howes, O.,; McCutcheon, R.,; Stone, J., J. Psychopharmacol. (London, UK) 2015, 29, 97–115/111–197–115/119, 119.
5. Carli, M.,; Invernizzi, R. W., Front. Neural Circuits 2014, 8, 58/51–58/20, 20.
6. Leyton, M.,; Vezina, P., Trends Pharmacol. Sci. 2014, 35, 268–276.
7. Gamage, N.,; Barnett, A.,; Hempel, N.,; Duggleby, R. G.,; Windmill, K. F.,; Martin, J. L.,; McManus, M. E., Toxicol. Sci. 2006, 90, 5–22.
8. Itaaho, K.,; Alakurtti, S.,; Yli-Kauhaluoma, J.,; Taskinen, J.,; Coughtrie Michael, W. H.,; Kostiainen, R., Biochem. Pharmacol. 2007, 74, 504–510.
9. Gomes, J.,; Grunau, A.,; Lawrence, A. K.,; Eberl, L.,; Gademann, K., Chem. Commun. (Cambridge, UK) 2013, 49, 155–157.
10. Belitsky, J. M.,; Lye, D. S.,; Gittleman, H. R.,; Gorlin, T. A.,; Gorham, A. N.,; Moore, C. A.,; Chaves, M. B.,; Ellowitz, M. Z., Supramol. Chem. 2014, 26, 233–244.
11. Moulay, S., Polym. Rev. (Philadelphia, PA, US) 2014, 54, 436–513.
12. Hu, H.,; Dyke, J. C.,; Bowman, B. A.,; Ko, C.-C.,; You, W., Langmuir 2016, 32, 9873–9882.
13. Bigler, D. J.,; Peterson, L. W.,; Cafiero, M., Comput. Theor. Chem. 2015, 1051, 79–92.
14. Hatstat, A. K.,; Morris, M.,; Peterson, L. W.,; Cafiero, M., Comput. Theor. Chem. 2016, 1078, 146–162.
15. Shafiq, Z.,; Cui, J.,; Pastor-Perez, L.,; San Miguel, V.,; Gropeanu, R. A.,; Serrano, C.,; del Campo, A., Angew. Chem. Int. Ed. 2012, 51, 4332–4335, S4332/4331–S4332/4337.
16. Louafi, F.,; Hurvois, J.-P.,; Chibani, A.,; Roisnel, T., J. Org. Chem. 2010, 75, 5721–5724.
17. Milhazes, N.,; Cunha-Oliveira, T.,; Martins, P.,; Garrido, J.,; Oliveira, C.,; Rego, A. C.,; Borges, F., Chem. Res. Toxicol. 2006, 19, 1294–1304.
18. Wang, B.,; Qin, L.,; Neumann, K. D.,; Uppaluri, S.,; Cerny, R. L.,; Di Magno, S. G., Org. Lett. 2010, 12, 3352–3355.
19. Johannes, M.,; Altmann, K.-H., Org. Lett. 2012, 14, 3752–3755.
20. Laudien, J.,; Fouquet, E.,; Zakri, C.,; Felpin, F.-X., Synlett 2010, 10, 1539–1543.
21. Davidson, J. P.,; Corey, E. J., J. Am. Chem. Soc. 2003, 125, 13486–13489.
22. Ivanov, I.,; Nikolova, S.,; Aladjov, D.,; Stefanova, I.,; Zagorchev, P., Molecules 2011, 16, 7019–7042.
23. Ettaoussi, M.,; Sabaouni, A.,; Rami, M.,; Boutin, J. A.,; Delagrange, P.,; Renard, P.,; Spedding, M.,; Caignard, D.-H.,; Berthelot, P.,; Yous, S., Eur. J. Med. Chem. 2012, 49, 310–323.
24. Zabjek, A.,; Petric, A., Tetrahedron Lett. 1999, 40, 6077–6078.
25. Soerensen, A.,; Rasmussen, B.,; Pittelkow, M., J. Org. Chem. 2015, 80, 3852–3857.
26. Kara, Y. S., Spectrochim. Acta Part A 2015, 151, 723–730.
27. Hansch, C.,; Leo, A.,; Taft, R. W., Chem. Rev. 1991, 91, 165–195.