Ritter reaction in subcritical water: An efficient and green method for amides synthesis

Letters in Organic Chemistry

Volumn 9, Issue 1, 2012, Pages 24-28

  Jiang, Shengqian ^a   Wang, Zhouyu ^a   Jiang, Zhenju ^a   Li, Jianhui ^a   Zhou, Shulin ^a   Pu, Long ^a  

^a XIHUA UNIVERSITY   (China)

Author keywords

Alcohol; Amide; Nitrile; Ritter reaction; Subcritical water; Trifluoromethanesulfonic acid

Indexed keywords

EID: 84858978791     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017812799304006     Document Type: Article

References (40)

1. (a) Ritter, J. J.; Minieri, P. P. A new reaction of nitriles, I: Amides from alkenes and mononitriles. J. Am. Chem. Soc., 1948, 70, 4045-4048;
2. (b) Ritter, J. J.; Kalish, J. A new reaction of nitriles, II: Synthesis of t-carbinamines. J. Am. Chem. Soc., 1948, 70, 4048-4050.
3. (a) Stavber, S.; Pecǎn, T. S.; Papež, M.; Zupan, M. Ritter-type fluorofunctionalisation as a new, effective method for conversion of alkenes to vicinal fluoroamides. Chem. Commun., 1996, 2247-2248; (Pubitemid 126679230)
4. 2-symmetric bis(oxazolines). Tetrahedron Lett., 1996, 37, 813-814; (Pubitemid 26047069)
5. (c) Goanvic, D. L.; Lallemand, M. C.; Tillequin, F.; Martens, T. A new and efficient electrochemical ring opening of 7-oxanorbornene systems via a modified Ritter reaction: direct approach to bicyclic valienamine analogues. Tetrahedron Lett., 2001, 42, 5175-5177; (Pubitemid 32635120)
6. (d) Nair, V.; Rajan, R.; Rath, N. P. A CAN-induced cyclodimerization- Ritter trapping strategy for the one-pot synthesis of 1-amino-4-aryltetralins from styrenes. Org. Lett., 2002, 4, 1575-1577;
7. (e) Penner, M.; Schweizer, F. Ritter-based glycoconjugation of amino acids and peptides-access to novel glycoconjugates displaying α,β-amide linkage between amino acid and sugar moiety. Carbohyd. Res. 2006, 342, 7-15; (Pubitemid 44917940)
8. (f) Pinto, R. M. A.; Salvador, J. A. R.; Roux, C. L. Ritter reaction mediated by Bismuth(III) salts: onestep conversion of epoxides into vic-acylamino-hydroxy compounds. Synlett., 2006, 2047-2050; (Pubitemid 44318213)
9. (g) Song, X. Z.; Hollingsworth, R. I. 1,3-dioxonium cation facilitated Ritter-type reaction: facile synthesis of protected aminopolyols. Tetrahedron Lett., 2006, 47, 229-232; (Pubitemid 41751073)
10. (h) Castellanos, L.; Duque, C.; Rodríguez, J. R.; Jiménez, C. Stereoselective synthesis of (-)-4-epiaxinyssamine. Tetrahedron., 2007, 63, 1544-1552; (Pubitemid 46074122)
11. (i) Morgan, I. R.; Yazici, A.; Pyne, S. G.; Skelton, B. W. Diastereoselective Ritter reaction of chiral cyclic N-acyliminium ions: synthesis of pyrido- and pyrrolo[2,3-d]oxazoles and 4-hydroxy-5- Nacylaminopyrrolidines and 5-hydroxy-6-N-acylaminopiperidines. J. Org. Chem., 2008, 73 , 2943-2946; (Pubitemid 351483017)
12. 3-containing oxirane for an access to central units of protease inhibitors. Tetrahedron Lett., 2009, 50, 857-859;
13. (k) Narayanan, C. R.; Kulkarnl, A. K.; Landge, A. B.; Wadia, M. S. One-step conversion of epoxides into via-acylamino-hydroxy compounds. Synthesis., 1977, 35-36.
14. Mukhopadhyay, M.; Reddy, M. M.; Maikap, G. C.; Iqbal, J. Cobalt(II)-catalyzed conversion of allylic alcohols/acetates to allylic amides in the presence of nitriles. J. Org. Chem., 1995, 60 , 2670-2676.
15. 3+- montmorillonite K10: an efficient catalyst for selective amidation of alcohols with nitriles under non-aqueous condition. Synth. Commun., 2000, 30, 821-827. (Pubitemid 30158150)
16. Sanz, R.; Martínez, A.; Guilarte, V.; Álvarez- Gutiérrez, J. M.; Rodríguez, F. The Ritter reaction under truly catalytic Brønsted acid conditions. Eur. J. Org. Chem., 2007, 4642-4645.
17. Firouzabadi, H.; Sardarian, A. R.; Badparva, H. Highly selective amidation of benzylic alcohols with nitriles. A modified Ritter reaction. Synth. Commun., 1994, 24, 601-607. (Pubitemid 24121041)
18. Yamato, T.; Hu, J. Y.; Shinoda, N. Perfluorinated sulfonic acid resin (Nafion-H) catalysed Ritter reaction of benzyl alcohols. J. Chem. Res., 2007, 641-643.
19. Habibi, Z.; Salehi, P.; Zolfigol, M. A.; Yousefi, M. A novel one-pot synthesis of unsymmetrical acyclic imides. Synlett., 2007, 5, 812-814. (Pubitemid 46509420)
20. Barbero, M.; Bazzi, S.; Cadamuro, S.; Dughera, S. o-Benzenedisulfonimide as a reusable brønsted acid catalyst for Ritter-type reactions. Eur. J. Org. Chem., 2009, 430-436.
21. 3-catalyzed Ritter reaction. synthesis of amides. Tetrahedron Lett., 2009, 50, 3470-3473.
22. Theerthagiri, P.; Lalitha, A.; Arunachalam, P. N. Iodine-catalyzed one-pot synthesis of amides from nitriles via Ritter reaction. Tetrahedron Lett., 2010, 51, 2813-2819.
23. (a) Bi, N. M.; Ren, M. G.; Song, Q. H. Photo-Ritter reaction of arylmethyl bromides in acetonitrile. Synth. Commun., 2010, 40, 2617-2623;
24. (b) Abe, T.; Takeda, H.; Miwa, Y.; Yamada, K.; Yanada, R.; Ishikura, M. Copper-catalyzed Ritter-type reaction of unactivated alkenes with dichloramine-T. Helv. Chim. Acta., 2010, 93, 233-241.
25. (c) Khazaei, A.; Zolfigol, M. A.; Moosavi-Zare, A. R.; Zare, A,; Parhami, A.; Khalafi-Nezhad, A. Trityl chloride as an efficient organic catalyst for the synthesis of 1-amidoalkyl-2-naphtols in neutral media at romm temperature. Appl. Catal. A: Gen., 2010, 386, 179-187;
26. (d) Ma'mani, L.; Heydari, A.; Sheykhan. M. The Ritter reaction under incredibly green protocol: Nano magnetically silica-supported Brønsted acid catalyst. Appl. Catal. A: Gen., 2010, 384, 122-127.
27. 2 as a mild and versatile reagent for Ritter amidation of olefins: a facile synthesis of secondary amides. Tetrahedron Lett., 2010, 51, 4827-4829.
28. (f) Callens, E.; Burton, A. J.; Barrett, A. G. M. Synthesis of amides using the Ritter reaction with bismuth triflate catalysis. Tetrahedron Lett., 2006, 47, 8699-8701. (Pubitemid 44648225)
29. (a) Savage, P. E. Organic chemical reactions in supercritical water. Chem. Rev., 1999, 99, 603-622;
30. (b) Akiya, N.; Savage, P. E. Roles of water for chemical reactions in high-temperature water. Chem. Rev., 2002, 102, 2725-2750; (Pubitemid 35381647)
31. (c) Chanda, A.; Fokin, V. V. Organic synthesis "on water". Chem. Rev., 2009, 109 , 725-748;
32. (d) Butler, R. N.; Coyne, A. G. Nature's reaction enforcer-comparative effects for organic synthesis "in water" and "on-water". Chem. Rev., 2010, 110, 6302-6337.
33. 40 ) as a highly efficient catalyst for the amidation of alcohols and protected alcohols with nitriles in water: A modified Ritter reaction. Catal. Commun., 2008, 9, 529-531. (Pubitemid 350181625)
34. (a) Jennings, J. M.; Bryson, T. A.; Gibson, J. M. Catalytic reduction in subcritical water. Green Chem., 2000, 2, 87-88.
35. (b) Sato, M.; Otabe, N.; Tuji, T.; Matsushima, K.; Kawanami, H.; Chatterjee, M.; Yokoyama, T.; Ikushima, Y.; Suzuki, T. M. Highlyselective and high-speed Claisen rearrangement induced with subcritical water microreaction in the absence of catalyst. Green Chem., 2009, 11, 763-766.
36. (c) Wang, G.; Li, C. J.; Li, J.; Jia, X. S. Catalyst-free water-mediated N-Boc deprotection. Tetrahedron Lett., 2009, 50, 1438-1440;
37. (d) Yuksel, A.; Sasaki, M.; Goto, M. Electrolysis reaction pathway for lactic acid in subcritical water. Ind. Eng. Chem. Res., 2011, 50, 728-734.
38. Other references about the synthesis of amides: (a) De, C. K.; Klauber, E. G.; Seidel, D. Merging nucleophilic and hydrogen bonding catalysis: An anion binding approach to the kinetic resolution of amines. J. Am. Chem. Soc., 2009, 131, 17060-17061.
39. (b) Harrison, P.; Meek, G. A complementary method to obtain Nacyl enamides using the Heck reaction: extending the substrate scope for asymmetric hydrogenation. Tetrahedron Lett., 2004, 45, 9277-9280. (Pubitemid 39491165)
40. (c) Gridnev, H. D.; Yasutake, M.; Higashi, N.; Imamoto, T. Asymmetric hydrogenation of enamides with Rh-BisP* and Rh-MiniPHOS catalysts. Scope. J. Am. Chem. Soc., 2001, 123, 5268-5276. (Pubitemid 32910669)