Erbium(III) chloride in ethyl lactate as a smart ecofriendly system for efficient and rapid stereoselective synthesis of trans-4,5-diaminocyclopent-2- enones

ACS Sustainable Chemistry and Engineering

Volumn 1, Issue 5, 2013, Pages 541-544

  Procopio, Antonio ^a   Costanzo, Paola ^a   Curini, Massimo ^b   Nardi, Monica ^c   Oliverio, Manuela ^a   Sindona, Giovanni ^c  

^a Dipartimento di Scienze della Salute   (Italy)

^b UNIVERSITY OF PERUGIA   (Italy)

^c UNIVERSITY OF CALABRIA   (Italy)

Author keywords

Diaminocyclopent 2 enones; Erbium(III) chloride; Ethyl lactate; Furfural

Indexed keywords

DIAMINOCYCLOPENT-2-ENONES; ECO-FRIENDLY; ETHYL LACTATE; FUNCTIONALIZED; STEREOSELECTIVE SYNTHESIS; SYNTHETIC INTERMEDIATES;

ALDEHYDES; FURFURAL; REACTION INTERMEDIATES; STEREOCHEMISTRY; STEREOSELECTIVITY;

ERBIUM;

EID: 84884213234     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/sc4000219     Document Type: Article

References (37)

1. Du Bois, D. J. CCR-3 Receptor Antagonists V. WO Patent 2003022799, 2003.
2. Szmuszkovicz, J.; Von Voigtlander, P. F.; Kane, M. P. A new nontricyclic antidepressant agent. Synthesis and activity of N-[trans-2- dimethylaminocyclopentyl]-N-(3,4-dichlorophenyl)propanamide and related compounds. J. Med. Chem. 1981, 24, 1230-1236.
3. Suzuki, T.; Onda, K.; Murakami, T.; Negoro, K.; Yahiro, K.; Maruyama, T.; Shimaya, A.; Ohta, M. WO Patent 2000076980, 2000.
4. Ohta, T.; Komoriya, S.; Yoshino, T.; Uoto, K.; Nakamoto, Y.; Naito, H.; Mochizuki, A.; Nagata, T.; Kanno, H.; Haginoya, N.; Yoshikawa, K.; Nagamochi, M.; Kobayashi, S.; Ono, M. A Preparation of Diamine Derivatives, Useful as FXa Inhibitors (Anticoagulants). U.S. Patent 2005020645, 2005.
5. Riley, D. P.; Henke, S. L.; Lennon, P. J.; Weiss, R. H.; Neumann, W. L.; Rivers, W. J.; Aston, K. W.; Sample, K. R.; Rahman, H.; Ling, C.-S.; Shieh, J.-J.; Busch, D. H.; Szulbinski, W. Synthesis, characterization, and stability of manganese(II) C-substituted 1,4,7,10,13-pentaazacyclopentadecane complexes exhibiting superoxide dismutase activity. Inorg. Chem. 1996, 35, 5213-5231.
6. D'Ambrosio M.; Guerriero, A.; Debitus, C.; Ribes, O.; Pusset, J.; Leroy, S.; Pietra, F. Agelastatin a, a new skeleton cytotoxic alkaloid of the oroidin family. Isolation from the axinellid sponge Agelas dendromorpha of the coral sea. J. Chem. Soc., Chem. Commun. 1993, 1305-1306.
7. Guerriero, A.; D'Ambrosio, M.; Chiasera, G.; Pietra, F. Conformational preferences and absolute configuration of agelastatin A, a cytotoxic alkaloid of the axinellid sponge Agelas dendromorpha from the Coral Sea, via combined molecular modelling, NMR, and exciton splitting for diamide and hydroxyamide derivatives. Helv. Chim. Acta 1994, 77, 1895-1902.
8. Hong, T. W.; Jimenez, D. R.; Molinski, T. F. Agelastatins C and D, new pentacyclic bromopyrroles from the sponge Cymbastela sp., and potent arthropod toxicity of (-)-agelastatin A. J. Nat. Prod. 1998, 61, 158-161.
9. Gonzales-Sabín, J.; Rebolledo, F.; Gotor, V. trans-Cyclopentane-1, 2-diamine: The second youth of the forgotten diamine. Chem. Soc. Rev. 2009, 38, 1916-1925.
10. Hofmann, T. Characterization of the chemical structure of novel colored maillard reaction products from furan-2-carboxaldehyde and amino acids. J. Agric. Food Chem. 1998, 46, 932-940.
11. Domostoj, M. M.; Irving, E.; Scheinmann, F.; Hale, K. J. New total synthesis of the marine antitumour alkaloid (-)-agelastatin A. Org. Lett. 2004, 6, 2615-2618.
12. Davis, F. A.; Deng, J. Asymmetric total synthesis of (-)-agelastatin a using sulfinimine (N-sulfinyl imine) derived methodologies. Org. Lett. 2005, 7, 621-623 (and references citated therein).
13. Lewis, K. G.; Mulquiney, C. E. Aspects of the formation and use of stenhouse salts and related compounds. Tetrahedron 1977, 33, 463-475.
14. Nicholson, E. S.; Ashworth, B. T. U.S. Patents 4013720, 19770722, 1977.
15. Lewis, K. G.; Mulquiney, C. E. Rearrangements in the furan series. II. The reaction between furfuraldehyde and aromatic amines. Aust. J. Chem. 1979, 32, 1079-1092.
16. McGowan J. C. The preparation of bases from the coloured compounds formed by condensation of furfuraldehyde with aromatic amines. J. Chem. Soc. 1949, 777-779.
17. Rombaut, J.; Smets, G. Azomethines III. Derives du furfuraldehyde. Bull. Soc. Chim. Belg. 1949, 58, 421-431.
18. Lewis, K. G.; Mulquiney, C. E. Rearrangements in the furan series. I. The reaction between furfuraldehyde and aniline. Aust. J. Chem. 1970, 23, 2315-2323.
19. Li S.-W.; Batey, R. A. Mild lanthanide(III) catalyzed formation of 4,5-diaminocyclopent-2-enones from 2-furaldehyde and secondary amines: A domino condensation/ring-opening/electrocyclization process. Chem. Commun. 2007, 3759-3761.
20. Ramesh, D.; Reddy, T. S.; Narasimhulu, M.; Rajaram, S.; Suryakiran, N.; Mahesh, K. C.; Venkateswarlu, Y. Efficient and rapid stereoselective synthesis of trans-4,5-diaminocyclopent-2-enones by acidic ionic liquid under solvent-free conditions. Chem. Lett. 2009, 38, 586-587.
21. Procopio, A.; Dalpozzo, R.; De Nino, A.; Maiuolo, L.; Nardi, M.; Russo, B. Synthesis of acetonides from epoxides catalyzed by Erbium(III) triflate. Adv. Synth. Catal. 2005, 347, 1447-1450.
22. Procopio, A.; Dalpozzo, R.; De Nino, A.; Maiuolo, L.; Nardi, M.; Romeo, G. Mild and efficient method for the cleavage of benzylidene acetals by using erbium (III) triflate. Org. Biomol. Chem. 2005, 3, 4129-4133.
23. Procopio, A.; Gaspari, M.; Nardi, M.; Oliverio, M.; Tagarelli, A.; Sindona, G. Simple and efficient MW-assisted cleavage of acetals and ketals in pure water. Tetrahedron. Lett. 2007, 48, 8623-8627.
24. Procopio, A.; Dalpozzo, R.; De Nino, A.; Maiuolo, L.; Oliverio, M.; Russo, B.; Tocci, A. Er(III) chloride: A very active acylation catalyst. Aust. J. Chem. 2007, 60, 75-79.
25. Procopio, A.; Gaspari, M.; Nardi, M.; Oliverio, M.; Rosati, O. Highly efficient and versatile chemoselective addition of amines to epoxides in water catalyzed by erbium(III) triflate. Tetrahedron. Lett. 2008, 49, 2289-2293.
26. Procopio, A.; Gaspari, M.; Nardi, M.; Oliverio, M.; Romeo, R. MW-assisted Er(OTf)3-catalyzed mild cleavage of isopropylidene acetals in Tricky substrates. Tetrahedron. Lett. 2008, 49, 1961-1964.
27. Bortolini, O.; De Nino, A.; Garofalo, A.; Maiuolo, L.; Procopio, A.; Russo, B. Erbium triflate in ionic liquids: A recyclable system of improving selectivity in Diels-Alder reactions. Appl. Catal., A 2010, 372, 124-129.
28. Frontier, A. J.; Collison, C. The Nazarov cyclization in organic synthesis. Recent avances. Tetrahedron 2005, 61, 7577-7606.
29. Pereira, C. S. M.; Silva, V. M. T. M.; Rodrigues, A. E. Ethyl lactate as a solvent: Properties, applications and production processes-a review. Green Chem. 2011, 13, 2658-2671.
30. Pham, T. P. T.; Cho, C.-W.; Yun, Y.-S. Environmental fate and toxicity of ionic liquids: A review. Water Res. 2010, 44, 352-372.
31. Zhao, D.; Liao, Y.; Zhang, Z. Toxicity of ionic liquids. Clean: Soil, Air, Water 2007, 35, 42-48.
32. Petkovic, M.; Seddon, K. R.; Rebelo, L. P. N.; Pereira, C. S. Ionic liquids: A pathway to environmental acceptability. Chem. Soc. Rev. 2011, 40, 1383-1403.
33. Warner, J. C.; Cannon, A. S.; Dye, K. M. Green chemistry. Environ. Impact Assess. Rev. 2004, 24, 775-799.
34. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford Science Publications: New York, 1998.
35. Bowner, C. T.; Hooftman, R. N.; Hanstveit, A. O.; Venderbosch, P. W. M.; van der Hoeven, N. The ecotoxicity and the biodegradability of lactic acid, alkyl lactate esters and lactate salts. Chemosphere 1998, 37, 1317-1333.
36. Clary, J. J.; Feron, V. J.; van Velthuijsen, J. A. Safety assessment of lactate esters. Regul. Toxicol. Pharmacol. 1998, 27, 88-97.
37. ErCl3 is less toxic than table salt: Oral mouse LD50 for ErCl3 and NaCl from Sigma-Aldrich security sheets are 4417 and 4000 mg kg-1. Prices for ErCl3 and Er(OTf)3 are 79.10 and 219,50 (for 25 g), respectively.