Methods for the direct synthesis of benzoxazoles from halogenated nitriles in alcoholic solvents

ACS Sustainable Chemistry and Engineering

Volumn 1, Issue 5, 2013, Pages 545-548

  Lester, Roy P ^a   Camp, Jason E ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Alcoholic solvent; Green chemistry; Heterocycle; Multifaceted catalysis; Platinum catalysis

Indexed keywords

2-AMINOPHENOLS; ALCOHOLIC SOLVENTS; DIRECT SYNTHESIS; GREEN CHEMISTRY; HETEROCYCLES; INCREASED FLEXIBILITY; REACTION CONDITIONS; ROBUST SYNTHESIS;

CATALYSIS; CYANIDES; FUNCTIONAL GROUPS; HALOGENATION; PLATINUM;

SOLVENTS;

EID: 84880256357     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc4000253     Document Type: Article

References (46)

1. Hisano, T.; Ichikawa, M.; Tsumoto, K.; Tasaki, M. Synthesis of benzoaxazoles, benzothiazoles and benzimidazoles and evaluation of their antifungal, insecticidal and herbicidal activities. Chem. Pharma. Bull. 1982, 30, 2996-3004.
2. Cantello, B. C. C.; Cawthorne, M. A.; Cottam, G. P.; Duff, P. T.; Haigh, D.; Hindley, R. M.; Lister, C. A.; Smith, S. A.; Thurlby, P. L. [[w-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents. J. Med. Chem. 1994, 37, 3977-3985.
3. Shi, D.-F.; Bradshaw, T. D.; Wrigley, S.; McCall, C. J.; Lelieveld, P.; Fichtner, I.; Stevens, M. F. G. Antitumor benzothiazoles. 3.1 Synthesis of 2-(4-aminophenyl)benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo. J. Med. Chem. 1996, 39, 3375-3384.
4. Kumar, D.; Jacob, M. R.; Reynolds, M. B.; Kerwin, S. M. Synthesis and evaluation of anticancer benzoxazoles and benzimidazoles related to UK-1. Bioorg. Med. Chem. 2002, 10, 3997-4004.
5. Clifford, D. P.; Edwards, R. V.; Hewson, R. T. Synthesis and plant growth regulatory properties of substituted 24 2,2,2-trichloroethylideneamino)phenols, 2-(trichloromethyl)benzoxazoles, and benzothiazoles. J. Agric. Food Chem. 1981, 29, 640-643.
6. Stephens F. F.; Bower, J. D. Preparation of benzimidazoles and benzoxazoles from Schiff bases. J. Chem. Soc. 1949, 2971-2972.
7. Hein, D. W.; Alheim, R. J.; Leavitt, J. J. The use of polyphosphoric acid in the synthesis of 2-aryl-and 2-alkyl-substituted benzimidazoles, benzoxazoles, and benzothiazoles. J. Am. Chem. Soc. 1957, 79, 427-429.
8. Evindar, G.; Batey, R. A. Parallel Synthesis of a Library of Benzoxazoles and Benzothiazoles Using Ligand-Accelerated Copper-Catalyzed Cyclizations of ortho-Halobenzanilides. J. Org. Chem. 2006, 71, 1802-1808.
9. Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Palladium-Catalyzed Arylation of Azole Compounds with Aryl Halides in the Presence of Alkali Metal Carbonates and the Use of Copper Iodide in the Reaction. Bull. Chem. Soc. Jpn. 1998, 71, 467-473.
10. Holan, G.; Samuel, E. L.; Ennis, B. C.; Hinde, R. W. 2- Trihalogenomethylbenzazoles. Part 1. Formation. J. Chem. Soc. C 1967, 20-25.
11. Holljes, E. L., Jr.; Wagner, E. C. Parallel Synthesis of a Library of Benzoxazoles and Benzothiazoles Using Ligand-Accelerated Copper-Catalyzed Cyclizations of ortho-Halobenzanilides. J. Org. Chem. 1944, 9, 31-49.
12. Kukushkin, V. Y.; Pombeiro, A. J. L. Additions to Metal-Activated Organonitriles. Chem. Rev. 2002, 102, 1771-1802.
13. Cobley, C. J.; van der Heuvel, M.; Abbadi, A.; de Vries, J. G. Platinum catalysed hydrolytic amidation of unactivated nitriles. Tetrahedron Lett. 2000, 41, 2467-2470.
14. Movassaghi, M.; Hill, M. D. Single-Step Synthesis of Pyrimidine Derivatives. J. Am. Chem. Soc. 2006, 128, 14254-14255.
15. Shen, H.; Xie, Z. Atom-Economical Synthesis of N-Heterocycles via Cascade Inter-/Intramolecular C-N Bond-Forming Reactions Catalyzed by Ti Amides. J. Am. Chem. Soc. 2010, 132, 11473-11480.
16. Tan H.; Pan, C.; Xu, Y.; Wang, H.; Pan, Y. Synthesis of benzoxazoles by the copper triflate catalysed reaction of nitriles and oaminophenols. J. Chem. Res. 2012, 370-373.
17. Kukushkin, V. Y.; Pombeiro, A. J. L. Metal-mediated and metalcatalyzed hydrolysis of nitriles. Inorg. Chim. Acta 2005, 358, 1-21.
18. Grivas, J. C.; Taurins, A. Reactions of trichloroacetonitrile with primary and secondary amines. I. Preparation of some trichloroacetamidines. Can. J. Chem. 1958, 36, 771-774.
19. See the Supporting Information for details.
20. Capello, C.; Fischer, U.; Hungerbuhler, K. What is a green solvent A comprehensive framework for the environmental assessment of solvents. Green Chem. 2007, 9, 927-934.
21. Jessop, P. G. Searching for green solvents. Green Chem. 2011, 13, 1391-1398.
22. For the related synthesis of amidines from trichloroacetonitrile, see: Oxley, P.; Partridge, M. W.; Short, F. W. 76. Amidines. Part VIII. Preparation of amidines from cyanides, ammonia or an amine, and an ammonium or substituted-ammonium salt. J. Chem. Soc. 1948, 303-309.
23. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Direct C-H transformation via iron catalysis. Chem. Rev. 2010, 111, 1293-1314.
24. Henderson, R. K.; C., J.-G.; Constable, D. J. C.; Alston, S. R.; Inglis, G. G. A.; Fisher, G.; Sherwood, J.; Binks, S. P.; Curzons, A. D. Expanding GSK's solvent selection guide-Embedding sustainability into solvent selection starting at medicinal chemistry. Green Chem. 2011, 13, 854-862.
25. For an example of the use of palladium(0)-catalyzed crosscoupling reactions in alcoholic solvent, see: Lygo, B.; Andrews, B. I. Enantioselective synthesis of aroylalanine derivatives. Tetrahedron Lett. 2003, 44, 4499-4502.
26. Ciriminna, R.; Pandarus, V.; Gingras, G.; Beland, F.; Cara, P. D.; Pagliaro, M. Heterogeneous Sonogashira coupling over nanostructured SiliaCat Pd(0). ACS Sustainable Chem. Eng. 2013, 1, 57-61.
27. For a review, see: Furstner, A. Gold and platinum catalysisa convenient tool for generating molecular complexity. Chem. Soc. Rev. 2009, 38, 3208-3221.
28. Flores A. F. C.; Brondani, S.; Pizzuti, L.; Martins, M. A. P.; Zanatta, N.; Bonacorso, H. G.; Flores, D. C. Haloacetylated Enol Ethers, 19: Synthesis of 3-(2-Thienyl)-and 3-(2-Furyl)-5-trihalomethyl Substituted Azoles. Synthesis 2005, 2744-2750.
29. Sczewski, F.; Tabin, P.; Tyacke, R. J.; Maconie, A.; Sscewski, J.; Kornicka, A.; Nutt, D. J.; Hudson, A. L. 2-(4,5-Dihydroimidazol-2-yl) benzimidazoles as highly selective imidazoline I2/adrenergic alpha2 receptor ligands. Bioorg. Med. Chem. 2006, 14, 6679-6685.
30. Since, M.; Khoumeri, O.; Verhaeghe, P.; Maillard-Boyer, M.; Terme, T.; Vanelle, P. First SNAr reaction using TDAE-initiated carbanions in quinazoline series. Tetrahedron Lett. 2011, 52, 3810-3813.
31. Dolzhenko, A. V.; Pastorin, G.; Dolzhenko, A. V.; Chui, W. K. A convenient method for the synthesis of 7-amino-substituted 1,2,4-triazolo[1,5-a] [1,3,5]triazin-5-amines. Tetrahedron Lett. 2008, 49, 7180-7183.
32. For example, reaction of trichlorobenzoxazole (2a) with pyrrolidine gave the substitution product 4 in an unoptimized 55% yield.
33. Mascal, M.; Modes, K. V.; Durmus, A. Concise photochemical synthesis of the antimalarial indole alkaloid decursivine. Angew. Chem., Int. Ed. 2011, 50, 4445-4446.
34. Mkosza, M.; Owczarczyk, Z. Reactions of organic anions. 161. Dihalomethylation of nitroarenes via vicarious nucleophilic substitution of hydrogen with trihalomethyl carbanions. J. Org. Chem. 1989, 54, 5094-5100.
35. El-Sheikh, M. I.; Marks, A.; Biehl, E. R. Investigation of the synthesis of benzoxazole via aryne reaction. J. Org. Chem. 1981, 46, 3256-3259.
36. Sbovata, S. M.; Bettio, F.; Marzano, C.; Mozzon, M.; Bertani, R.; Benetollo, F.; Michelin, R. A. Benzylamidine complexes of platinum(II) derived by nucleophilic addition of primary and secondary amines. X-ray crystal structure of trans-[PtCl2{Z-N(H)C(NHMe)CH2Ph}2]. Inorg. Chim. Acta 2008, 361, 3109-3116.
37. Lu, B.-L; Dai, L.; Shi, M. Strained small rings in gold-catalyzed rapid chemical transformations. Chem. Soc. Rev. 2012, 41, 3318-3339.
38. Britton, J.; Camp, J. E. Synthesis of heterocycles via gold multifaceted catalysis. Chem. Today 2012, 30 (Suppl), 6-8.
39. Penno, D.; Lillo, V.; Koshevoy, I. O.; Sanau, M.; Ubeda, M. A.; Lahuerta, P.; Fernandez, E. Multifaceted palladium catalysts towards the tandem diboration-arylation reactions of alkenes. Chem. Eur. J. 2008, 14, 10648-10655.
40. Perez, A. G.; Lopez, C. S.; Marco-Contelles, J.; Faza, O. N.; Soriano, E.; de Lera, A. R. Mechanism of the gold-catalyzed rearrangement of (3-acyloxyprop-1-ynyl)oxiranes: a dual role of the catalyst. J. Org. Chem. 2009, 74, 2982-2991.
41. Pubill-Ulldemolins, C.; Bonet, A.; Bo, C.; Gulyas, H.; Fernandez, E. A new context for palladium mediated -addition reaction: an open door to consecutive functionalization. Org. Biomol. Chem. 2010, 8, 2667-2682.
42. Ngwerume, S.; Camp, J. E. Gold-catalysed rearrangement of Ovinyl oximes for the synthesis of highly substituted pyrroles. Chem. Commun. 2011, 47, 1857-1859.
43. Ngwerume, S.; Lewis, W.; Camp, J. E. Development of a goldmultifaceted catalysis approach to the synthesis of highly substituted pyrroles: mechanistic insights via Huisgen cycloaddition studies. J. Org. Chem. 2013, 78, 920-934.
44. Blanc, A.; Tenbrink, K.; Weibel, J.-M.; Pale, P. Mechanistic studies and improvement of coinage metal-catalyzed transformation of alkynyloxiranes to furans: An alcohol addition-cyclization-elimination cascade. J. Org. Chem. 2009, 74, 5342-5348.
45. Kern, N.; Hoffman, M.; Blanc, A.; Weibel, J.-M.; Pale, P. Gold(I)-catalyzed rearrangement of N-aryl 2-alkynylazetidines to pyrrolo[1,2-a]indoles. Org. Lett. 2013, 15, 836-839.
46. Fogg, D. E.; dos Santos, E. N. Tandem catalysis: A taxonomy and illustrative review. Coord. Chem. Rev. 2004, 248, 2365-2379