Convenient synthesis of 1-arylmethyl-2-naphthols

Synthetic Communications

Volumn 37, Issue 6, 2007, Pages 877-888

  Paul, Nawal K ^a   Dietrich, Lindsay ^a   Jha, Amitabh ^a  

^a ACADIA UNIVERSITY   (Canada)

Author keywords

1 arylmethyl 2 naphthols; Deamination; Microwave; Pd catalyzed; Solvent free

Indexed keywords

1 (4 AMINOBENZYL) 2 NAPHTHOL; 1 (4 METHOXYBENZYL) 2 NAPHTHOL; 1 (4 METHYLBENZYL) 2 NAPHTHOL; 1 [(PYRIDIN 2 YL)METHYL] 2 NAPHTHOL; 1 [(PYRIDIN 4 YL)METHYL] 2 NAPHTHOL; 1 BENZYL 2 NAPHTHOL; 2 NAPHTHOL; MANNICH BASE; NAPHTHOL DERIVATIVE; PALLADIUM; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DEAMINATION; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MANNICH REACTION; MICROWAVE RADIATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 33847323906     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910601163547     Document Type: Article

References (35)

1. Schapira, M.; Abagyan, R.; Totrov, M. Nuclear hormone receptor targeted virtual screening. J. Med. Chem. 2003, 46, 3045-3059.
2. Harrison, I. T.; Lewis, B.; Nelson, P.; Rooks, W.; Roszkowski, A.; Tomolonis, A.; Fried, J. H. Nonsteroidal antiinflammatory agents, I: 6-Substituted 2-naphthylacetic acids. J. Med. Chem. 1970, 13, 203-205.
3. Goudie, A. C.; Gaster, L. M.; Lake, A. W.; Rose, C. J.; Freeman, P. C.; Hughes, B. O.; Miller, D. 4-(6-Methoxy-2-naphthyl)butan-2-one and related analogs, a novel structural class of antiinflammatory compounds. J. Med. Chem. 1978, 21, 1260-1264.
4. Hurwitz, P.; Thompson, J. M. Uses of naphazoline in ophthalmology. Arch. Ophthal. 1950, 43, 712-717.
5. Black, J. W.; Duncan, W. A.; Shanks, R. G. Comparison of some properties of pronethalol and propranolol. Br. J. Pharmacol. 1997, 120 (4 Suppl.), 285-299.
6. Gardner, F. E.; Marth, P. C.; Batjer, L. P. Spraying with plant growth substances to prevent apple fruit dropping. Science 1939, 90, 208-209.
7. Archer, T. E.; Stokes, J. D. Residue analysis of 2-naphthoxyacetic acid and 2-naphthol on field-sprayed tomatoes by high-pressure liquid chromatogaphy. J. Agric. Food. Chem. 1980, 28, 877-880.
8. Petranyi, G.; Ryder, N. S.; Stutz, A. Allylamine derivatives: New class of synthetic antifungal agents inhibiting fungal squalene epoxidase. Science 1984, 224, 1239-1241.
9. Kyle, A. A.; Dahl, M. V. Topical therapy for fungal infections. Am. J. Clin. Dermatol. 2004, 5, 443-451.
10. Duperray, B.; Chastrette, M.; Makabeh, M. C.; Pacheco, H. Analysis of bactericide activity for aliphatic-alcohols and beta-naphthols populations using Hansch and Darc-Pelco methods - Lengthening chain effect. Eur. J. Med. Chem. 1976, 11, 433-437.
11. Hardman, A. F. Treatment of rubber and product thereof. US Patent 2,375,168, 1945.
12. Behaghel, O.; Freiensehner, H. Rearrangement of phenol benzyl ethers at high temperatures. Chem. Ber. 1934, 67, 1368-1374.
13. Gomberg, M.; Buchler, C. C. The preparation of benzyl esters and other benzyl-derivatives from benzyl chloride. J. Am. Chem. Soc. 1920, 42, 2059-2072.
14. Setkina, V. N.; Kursanov, D. N. Exchange and cleavage reactions of quaternary ammonium salt, VIII: Reaction with alcohols and phenols of substituted ammonium salts with a benzyl radical. Izv. Akad. Nauk. SSSR, Ser. Khim. 1951, 81.
15. Cornforth, J. W.; Cornforth, R. H.; Robinson, R. Nuclear methylation of phenols by means of methanolic sodium methoxide. J. Chem. Soc. 1942, 682-684.
16. Curtin, D. Y.; Tuttes, R. C.; Dybvig D. H. Nuclear alkyation of salts of naphthols and anthranols. J. Org. Chem. 1960, 25, 155-158.
17. Badri, M.; Brunet, J. J.; Perron, R. Ionic liquids as solvents for the regioselective O-alkylation of C/O ambident nucleophiles. Tetrahedron Lett. 1992, 33, 4435-4438.
18. Bram, G.; Loupy, A.; SanSoulet, J.; Vaziri-Zand, F. Highly selective benzylations of β-naphthoxide anion in heterogeneous media. Tetrahedron Lett. 1984, 25, 5035-5038.
19. Bram, G.; Geraghty, M.; Nee, G.; Seyben-Penne, J. Regioselectivity of the alkylation of ambident anionic species on alumina or in the presence of solid hexamethylphosphoric triamide. J. Chem. Soc., Chem. Commun. 1980, 7, 325-326.
20. Smith, J. G.; Welankinwar, S. S.; Shandz, B. S.; Lai, E. H.; Chu, N. G. Synthetic routes to derivatives of polycyclic aromatic hydrocarbons using isobenzofurans as transient reactive intermediates. J. Org. Chem. 1980, 45, 1817-1824.
21. Katritzky, A. R.; Lan, X.; Lam, J. N. O-(alpha- Benzotriazolylalkyl)phenols: Versatile intermediates for the synthesis of substituted phenols. Chem. Ber. 1991, 124, 1809-1817.
22. Abdel-Wahab, A. -M. A.; Abdel-Rahman, A. E. Molecular rearrangements in alkyl aryl sulfides, part II: Pyrolysis of benzyl phenyl sulfide. Indian J. Chem. 1981, 20, 636-639.
23. Kito, T.; Yoshinaga, K.; Ohkami, S.; Ikeda, K.; Yamaye, M. Precursors in the alkylation of 2-naphthol with benzyl alcohol in the presence of a base. J. Org. Chem. 1985, 50, 4628-4630.
24. Desai, W. Naphthalene series, XIV: Preparation and properties of 2,4-distearoyl-, 2,4-dipalmitoyl-, and 2,4-dilauroyl-1-naphthols. Proc. Indian Acad. Sci. Sect. A. 1947, 24, 282-385.
25. Buu-Hoi, P. H.; Demerseman, P. Zinc chloride-calalyzed benzylations of phenols and naphthols. J. Org Chem. 1955, 20, 1129-1134.
26. Sagorewskii, V. A. The influence of the character of the reagent on the direction of reactions of O- and C-substitution in metallic derivatives of keto-enol systems. Zh. Obshch. Khim. 1958, 28, 488-494.
27. Elkobaisi, F. M.; Higginbottom, W. J. The course of the thermal rearrangement of benzyl phenyl ether. J. Chem. Soc. 1960, 1286-1291.
28. Kuhnert, N. Microwave-assisted reactions in organic synthesis - Are there any nonthermal microwave effects? Angew. Chem. Int. Ed. 2002, 41, 1863-1866.
29. Jha, A.; Paul, N. K.; Trikha, S.; Cameron, T. S. Novel synthesis of 2-naphthol Mannich bases and their NMR behavior. Can. J. Chem. 2006, 84, 843-853.
30. Jha, A.; Padmanilayam, M. P.; Dimmock, J. R. Conversion of substituted 1-arylidene-2-tetralones to 1-arylmethyl-2-alkoxynaphthalenes: An example of facile aromatization. Synthesis 2002, 463-465.
31. Jha, A.; Dimmock, J. R. Convenient, tandem and one-reaction vessel synthesis of mixed 1-alkyl-2-alkoxynaphthalenes fiom 2-tetralone. Can. J. Chem. 2003, 81, 293-296.
32. Jha, A.; Beal, J. Convinient one step synthesis of benzo[a,j]xanthenes from 2-tetralones. Tetrahedron Lett. 2004, 45, 8999-9001.
33. Sharifi, A.; Mirzaei, M.; Naimi-Jamal, M. R. Solvent-free aminoalkylation of phenols and indoles assisted by microwave irradiation. Monatsh. Chem. 2001, 132, 874-880.
34. Bose, A. K.; Manhas, M. S.; Ghosh, M.; Shah, M.; Raju, V. S.; Bari, S. S.; Newaz, S. N.; Banik, B. K.; Chaudhary, A. G.; Barakat, K. J. Microwave-induced organic reaction enhancement chemistry, 2: Simplified techniques. J. Org. Chem. 1991, 56, 6968-6970.
35. Katritzky, A. R.; Abdel-Fattah, A. A. A.; Tymoshenko, D. O.; Belyakov, S. A.; Ghiviriga, I.; Steel, P. J. Amino(hetero)arylmethylation of phenols with n-[-amino (hetero)-arylmethyl]benzotriazoles. J. Org. Chem. 1999, 64, 6071-6075.