Synthesis of new and novel N-protected 1-aminoalkyl-2-naphthol derivatives

Synthetic Communications

Volumn 39, Issue 14, 2009, Pages 2560-2574

  Shaterian, Hamid Reza ^a   Hosseinian, Asghar ^a   Ghashang, Majid ^a  

^a UNIVERSITY OF SISTAN AND BALUCHESTAN   (Iran)

Author keywords

2 naphthol; Carbamate; Heterogeneous catalyst; N protected 1 aminoalkyl 2 naphthol; Silica perchloric acid (HClO4 SiO2)

Indexed keywords

BENZYL (2 CHLOROPHENYL)(2 HYDROXYNAPHTHALEN 1 YL)METHYL CARBAMATE; BENZYL (2 HYDROXYNAPHTHALEN 1 YL)(3 METHOXYPHENYL)METHYL CARBAMATE; BENZYL (2 HYDROXYNAPHTHALEN 1 YL)(PHENYL)METHYL CARBAMATE; BENZYL (3 CHLOROPHENYL)(2 HYDROXYNAPHTHALEN 1 YL)METHYL CARBAMATE; BENZYL (4 FLUOROPHENYL)(2 HYDROXYNAPHTHALEN 1 YL)METHYL CARBAMATE; METHYL (2 HYDROXYNAPHTHALEN 1 YL)(3 NITROPHENYL)METHYL CARBAMATE; METHYL (2 HYDROXYNAPHTHALEN 1 YL)(4 NITROPHENYL)METHYL CARBAMATE; METHYL (2 HYDROXYNAPHTHALEN 1 YL)(PHENYL)METHYL CARBAMATE; METHYL (2,4 DICHLOROPHENYL)(2 HYDROXYNAPHTHALEN 1 YL)METHYL CARBAMATE; METHYL (2,5 DIMETHOXYPHENYL)(2 HYDROXYNAPHTHALEN 1 YL)METHYL CARBAMATE; METHYL (3 CHLOROPHENYL)(2 HYDROXYNAPHTHALEN 1 YL)METHYL CARBAMATE; METHYL (4 CHLOROPHENYL)(2 HYDROXYNAPHTHALEN 1 YL)METHYL CARBAMATE; NAPHTHOL DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SOLVENT EFFECT; SYNTHESIS;

EID: 67650290556     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802659194     Document Type: Article

References (23)

1. (a) Seebach, D.; Matthews, J. L. b-Peptides: A surprise at every turn. J. Chem. Soc., Chem. Commun. 1997, 2015-2022;
2. +)-negamycin from an acyclic homoallylamine by 1,3-asymmetric induction. J. Am. Chem. Soc.1982, 104, 6465-6466;
3. (c) Knapp, S. Synthesis of complex nucleoside antibiotics. Chem. Rev. 1995, 95, 1859-1876;
4. (d) Juaristi, E. In Enantioselective Synthesis of b-Amino Acids; John Wiley & Sons: New York, 1997.
5. (a) Dingermann, T.; Steinhilber, D.; Folkers, G. In Molecular Biology in Medicinal Chemistry; Wiley-VCH, Weinheim, Germany, 2004;
6. (b) Shen, A. Y.; Tsai, C. T.; Chen, C. L. Synthesis and cardiovascular evaluation of N-substituted 1-aminomethyl-2-naphthols. Eur. J. Med. Chem. 1999, 34, 877-882.
7. (a) Welch, W. M.; Kraska, A. R.; Sarges, R.; Koe, B. K. Nontricyclic antidepressant agents derived from cis- and trans-1-amino-4-aryltetralins. J. Med. Chem. 1984, 27, 1508-1515;
8. (b) Corey, E. J.; Gant, T. G. A catalytic enantioselective synthetic route to the important antidepressant sertraline. Tetrahedron Lett. 1994, 35, 5373-5376;
9. (c) Chen, C.; Reamer, R. A. Efficient enantioselective synthesis of sertraline, a potent antidepressant, via a novel intramolecular nucleophilic addition to imine. Org. Lett. 1999, 1, 293-294;
10. +)-sertraline. Org. Lett. 1999, 1, 233-236.
11. For representative examples, see (a) Enders, D.; Muller, S. F.; Raabe, G. Enantioselective synthesis of b-amino sulfones by aza-Michael addition to alkenyl sulfones. Angew. Chem., Int. Ed. 1999, 38, 195-197;
12. (b) Evans, D. A.; Wu, L. D.; Wiener, J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. A general method for the synthesis of enantiomerically pure b-substituted, b-amino acids through a-substituted succinic acid derivatives. J. Org. Chem.1999, 64, 6411-6417;
13. (c) Kochi, T.; Tang, T. P.; Ellman, J. A. Asymmetric synthesis of syn- and anti-1,3-amino alcohols. J. Am. Chem. Soc. 2002, 124, 6518-6519;
14. (d) Murai, T.; Sano, H.; Kawai, H.; Aso, H.; Shibahara, F. NThioacyl 1,3-amino alcohols: Synthesis via ring-opening of oxiranes with thioamide dianions and applications as key intermediates leading to stereochemically defined 5,6-dihydro-4H-1,3-oxazines and 1,3-amino alcohols. J. Org. Chem. 2005, 70, 8148-8153;
15. (e) Keck, G. E.; Truong, A. P. Directed reduction of b-amino ketones to syn or anti-1,3-amino alcohol derivatives. Org. Lett. 2002, 4, 3131-3134;
16. (f) Ohno, H.; Hamaguchi, H.; Tanaka, T. Umpolung of chiral 2-Ethynylaziridines: Indium(I)-mediated stereoselective synthesis of nonracemic 1,3-amino alcohols bearing three chiral centers, catalyzed by palladium(0). Org. Lett. 2000, 2, 2161-2163.
17. Green, W.; Wats, M. P. G. Protecting Groups in Organic Synthesis; 2nd ed.; John Wiley and Sons: New York, 1999.
18. (a) Chakraborti, A. K.; Gulhane, R. Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines. Chem. Commun. 2003, 1896-1897;
19. (b) Chakraborti, A. K.; Gulhane, R. Indian Patent 266=DEL=2003, March 10, 2003;
20. (c) Shaterian, H. R.; Shahrekipoor, F.; Ghashang, M. Silica-supported perchloric acid (HClO4-SiO2): A highly efficient and reusable catalyst for the protection of hydroxyl groups using HMDS under mild and ambient conditions. J. Mol. Catal. A: Chem. 2007, 272, 142-151;
21. (d) Kamble, V. T.; Jamode, V. S.; Joshi, N. S.; Biradara, A. V.; Deshmukh, R. Y. An efficient method for the synthesis of acylals from aldehydes using silica-supported perchloric acid (HClO4-SiO2). Tetrahedron Lett. 2006, 47, 5573-5576;
22. (e) Mukherjee, C.; Misra, A. K. Glycosylation and pyranose-furanose isomerization of carbohydrates using HClO4- SiO2: Synthesis of oligosaccharides containing galactofuranose. Synthesis2007, 683-692;
23. (f) Shaterian, H. R.; Yarahmadi, H.; Ghashang, M. Silicasupported perchloric acid (HClO4-SiO2): An efficient and recyclable heterogeneous catalyst for the one-pot synthesis of amidoalkyl naphthols. Tetrahedron 2008, 64, 1263-1269.