Facile synthesis of symmetrical bis(benzhydryl)ethers using p-toluenesulfonyl chloride under solvent-free conditions
Tóm tắt
The benzhydryl ether moiety is widely distributed in nature and constitutes a key structural motif in numerous molecules of significant biological potential and of prospective clinical uses. Solvent-free and cost-effective facile synthesis of symmetrical bis(benzhydryl)ethers is, thus, much desirable. A simple and efficient method for the facile synthesis of symmetrical bis(benzhydryl)ethers directly from the corresponding benzhydrols has been developed using a catalytic amount of p-toluenesulfonyl chloride (5 mol%) at an oil bath temperature of 110°C under solvent-free conditions. Operational simplicity, low reagent loading, high product yields, short reaction time, and solvent-free conditions are the notable advantages of the present method.
Tài liệu tham khảo
Brahmachari G: Handbook of pharmaceutical natural products. 1st edition. Weinheim: Wiley-VCH; 2010.
Li X, Upton TG, Gibb CLD, Gibb BC: Resorcinarenes as templates: a general strategy for the synthesis of large macrocycles. J Am Chem Soc 2003, 125: 650–651. 10.1021/ja029116g
Ley SV, Thomas AW: Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation. Angew Chem Int Ed 2003, 42: 5400–5449. 10.1002/anie.200300594
Tlili A, Monnier F, Taillefer M: Selective one-pot access to symmetrical or unsymmetrical diaryl ethers by copper-catalyzed double arylation of a simple oxygen source. Chem Eur J 2010, 16: 12299–12302. 10.1002/chem.201001373
Tan ES, Miyakawa M, Bunzow JR, Grandy DK, Scanlan TS: Exploring the structure-activity relationship of the ethylamine portion of 3-iodothyronamine for rat and mouse trace amine-associated receptor 1. J Med Chem 2007, 50: 2787–2798. 10.1021/jm0700417
Nicolaou KC, Boddy CNC, Brase S, Winssinger N: Chemistry, biology and medicine of the glycopeptide antibiotics. Angew Chem Int Ed 1999, 38: 2097–2152.
Harris CM, Kopecka H, Harris TM: Vancomycin: structure and transformation to CDP-I. J Am Chem Soc 1983, 105: 6915–6922. 10.1021/ja00361a029
Barna JCJ, Williams DH, Stone DJM, Leung TWC, Doddrell DM: Structure elucidation of the teicoplanin antibiotics. J Am Chem Soc 1984, 106: 4895–4902. 10.1021/ja00329a044
Hayashi M: Drug Data Report 704 (JP 97077745). Barcelona: J. R. Prous Science; 1997.
Su D, Lim JJ, Tinney E, Wan B, Young MB, Anderson KD, Rudd D, Munshi V, Bahnck C, Felock PJ, Lu M, Lai M, Touch S, Moyer G, DiStefano DJ, Flynn JA, Liang Y, Sanchez R, Perlow-Poehnelt R, Miller M, Vacca JP, Williams TM, Anthony NJ: Biaryl ethers as novel non-nucleoside reverse transcriptase inhibitors with improved potency against key mutant viruses. J Med Chem 2009, 52: 7163–7169. 10.1021/jm901230r
Weis R, Schlapper C, Brun CR, Kaiser M, Seebacher W: Antiplasmodial and antitrypanosomal activity of new esters and ethers of 4-dialkylaminobicyclo[2.2.2]octan-2-ols. Eur J Pharm Sci 2006, 28: 361–368. 10.1016/j.ejps.2006.04.003
Van Der Zee P, Hespe W: A comparison of the inhibitory effects of aromatic substituted benzhydryl ethers on the uptake of catecholamines and serotonin into synaptosomal preparations of the rat brain. Neuropharmacol 1978, 17: 483–490. 10.1016/0028-3908(78)90054-0
Nilsson JL, Wågermark J, Dahlbom R: Potential antiparkinsonism agents. Quinuclidinyl benzhydryl ethers. J Med Chem 1969, 12: 1103–1105. 10.1021/jm00306a034
McGavack TH, Schulman PM, Boyd LJ: A clinical investigation of beta-morpholino-ethyl benzhydryl ether hydrochloride (linadryl) as an antihistamine agent. J Allergy 1948, 19: 141–145. 10.1016/0021-8707(48)90102-6
Loew ER, Kaiser ME: Alleviation of anaphylactic shock in guinea pigs with synthetic benzhydryl alkamine ethers. Exp Biol Med 1945, 58: 235–237.
Pyo MK, Jin JL, Koo YK, Yun-Choi S: Phenolic and furan type compounds isolated from Gastrodia elata and their anti-platelet effects. Arch Pharm Res 2004, 27: 381–385. 10.1007/BF02980077
Pitsinos EN, Vidali VP, Couladouros EA: Diaryl ether formation in the synthesis of natural products. Eur J Org Chem 2011, 7: 1207–1222.
Pratt EF, Draper JD: Reaction rates by distillation. I. The etherification of phenylcarbinols and the transetherification of their ethers1. J Am Chem Soc 1949, 71: 2846–2849. 10.1021/ja01176a075
Welch CM, Smith HA: The properties of benzhydrol in sulfuric acid solution. J Am Chem Soc 1950, 72: 4748–4750. 10.1021/ja01166a112
Smith HA, Thompson RG: Preparation and properties of substituted benzhydryl carbonium ions. J Am Chem Soc 1955, 77: 1778–1783. 10.1021/ja01612a018
Toda F, Takumi H, Akehi M: Efficient solid-state reactions of alcohols: dehydration, rearrangement, and substitution. J Chem Soc Chem Commun 1990, 1270–1271.
Brahmachari G, Laskar S: A very simple and highly efficient procedure for N -formylation of primary and secondary amines at room temperature under solvent-free conditions. Tetrahedron Lett 2010, 51: 2319–2322. 10.1016/j.tetlet.2010.02.119
Brahmachari G, Laskar S, Sarkar S: Metal acetate/metal oxide in acetic acid: an efficient reagent for the chemoselective N -acetylation of amines. J Chem Res 2010, 34: 288–295.
Brahmachari G, Laskar S, Sarkar S: A green approach to chemoselective N -acetylation of amines using catalytic amount of zinc acetate in acetic acid under microwave irradiation. Indian J Chem 2010, 49B: 1274–1281.
Brahmachari G, Das S: Bismuth nitrate-catalyzed multicomponent reaction for efficient and one-pot synthesis of densely functionalized piperidine scaffolds at room temperature. Tetrahedron Lett 2012, 53: 1479–1484. 10.1016/j.tetlet.2012.01.042
Brahmachari G, Banerjee B: A comparison between catalyst-free and ZrOCl 2 ·8H 2 O-catalyzed Strecker reactions for the rapid and solvent-free one-pot synthesis of racemic α-aminonitrile derivatives. Asian J Org Chem 2012, 1: 251–258.
Brahmachari G, Das S: One-pot synthesis of 3-[( N -alkylanilino)(aryl)methyl] indoles via a transition metal assisted three-component condensation at room temperature. J Het Chem 2013. in press
Brahmachari G, Das S: A simple and straightforward method for one-pot synthesis of 2,4,5-triarylimidazoles using titanium dioxide as an eco-friendly and recyclable catalyst under solvent-free conditions. Indian J Chem Sec B 2013, 52B: 387–393.
Sheldrick GM: SHELXS97, Program for the solution of crystal structures. Gottingen: University of Gottingen; 1997.
Farrugia LJ: ORTEP-3 for windows—a version of ORTEP-III with a graphical user interface (GUI). J Appl Cryst 1997, 30: 565–566.
Farrugia LJ: WinGX suite for small-molecule single-crystal crystallography. J Appl Cryst 1999, 32: 837–838. 10.1107/S0021889899006020
Nardelli M: PARST95-An update to PARST. A system of Fortran routines for calculating molecular structure parameters from the results of the crystal structure analysis. J Appl Cryst 1995, 28: 659. 10.1107/S0021889895007138
Spek AL: Structure validation in chemical crystallography. Acta Cryst 2009, D65: 148–155.
Koloves M, Froussios C: O -diphenylmethylation of alcohols and carboxylic acids using diphenylmethyl diphenyl phosphate as alkylating agent. Tetrahedron Lett 1984, 25: 3909–3912. 10.1016/S0040-4039(01)91201-8
Grummitt O, Buck AC: Di-(p, p′-dichlorobenzohydryl) ether. J Am Chem Soc 1945, 67: 693.
Welch CM, Smith HA: Reactions of carboxylic acids in sulfuric acid. J Am Chem Soc 1953, 75: 1412–1415. 10.1021/ja01102a042
