Synthesis of 2-oxazolines and 2-thiazolines using lanthanide amino alkoxide

Synthetic Communications

Volumn 37, Issue 18, 2007, Pages 3127-3142

  Padmavathi, V ^a   Reddy, B Chandra Obula ^a   Thriveni, P ^a   Mohan, A V Nagendra ^a  

^a SRI VENKATESWARA UNIVERSITY   (India)

Author keywords

cyclodextrin; 2 oxazolines; 2 thiazolines; SmCl3

Indexed keywords

2 OXAZOLINE DERIVATIVE; 2 THIAZOLINE DERIVATIVE; ESTER DERIVATIVE; LANTHANIDE; LANTHANIDE AMINO ALKOXIDE; OXAZOLINE DERIVATIVE; PHENACYSULFONYLACETIC ACID METHYL ESTER; UNCLASSIFIED DRUG;

ARTICLE; SYNTHESIS;

EID: 34548595270     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701545098     Document Type: Article

References (40)

1. (a) Jin, Z. Muscarine, imidazole, oxazole, thiazole alkaloids. Nat. Prod. Rep. 2003, 20, 584-605, and references there in;
2. (b) Lewis, J. R. Amaryllidaceae, sceletium, imidazole, oxazole, thiazole, peptide and miscellaneous alkaloids. Nat. Prod. Rep. 2002, 19, 223-258, and references there in.
3. (a) Wipf, P.; Miller, C. P. An investigation of the Mitsunobu reaction in the preparation of peptide oxazolines, thiazolines, and aziridines. Tetrahedron Lett. 1992, 33, 6267-6270;
4. (b) Phillips, A. J.; Uto, Y.; Wipf, P.; Reno, M. J.; Williams, D. R. Synthesis of functionalized oxazolines and oxazoles with DAST and Deoxo-Fluor. Org. Lett. 2000, 2, 1165-1168.
5. Meyers, A. I.; Slade, J. Asymmetric addition of organometallics to chiral keto-oxazolines. Preparation of enantiomerically enriched α-hydroxy acids. J. Org. Chem. 1980, 45, 2785-2791.
6. 2-thiazolines and 2-substituted benzoxazoles. Tetrahedron 1993, 49, 9353-9372;
7. (b) Cwik, A.; Hell, Z.; Hegedus, A.; Finta, Z.; Horvath, Z. A simple synthesis of 2-substituted oxazolines and oxazines. Tetrahedron Lett. 2002, 43, 3985-3987.
8. (a) Panek, J. S.; Masse, C. E. An improved synthesis of (4S,5S)-2-phenyl-4-(methoxycarbonyl)-5-isopropyloxazoline from (S)-phenylglycinol. J. Org. Chem. 1998, 63, 2382-2384;
9. (b) Kamata, K.; Agata, I.; Meyers, A. I. An efficient and versatile method for the synthesis of optically active 2-oxazolines: An acid-catalyzed condensation of ortho esters with amino alcohols. J. Org. Chem. 1998, 63, 3113-3116.
10. Oussaid, B.; Berlan, J.; Soufiaoui, M.; Garrigues, B. Improved synthesis of oxazoline under microwave irradiation. Synth. Commun. 1995, 25, 659-665.
11. Schumacher, D. P.; Clark, J. E.; Murphy, B. L.; Fischer, P. A. An efficient synthesis of florfenicol. J. Org. Chem. 1990, 55, 5291-5294.
12. (a) Charette, A. B.; Chua, P. Mild method for the synthesis of thiazolines from secondary and tertiary amides. J. Org. Chem. 1998, 63, 908-909;
13. (b) Busacca, C. A.; Dong, Y.; Spinelli, E. M.A. One step synthesis of thiazolines from esters. Tetrahedron Lett. 1996, 37, 2935-2938.
14. 2-thiazolines from n-acyl-2-aminoethanols. J. Am. Chem. Soc. 1935, 57, 1079-1080;
15. (b) Nishio, T. Sulfur-containing heterocycles derived by the reaction of hydroxyl amides and Lawesson's reagent. Tetrahedron Lett. 1995, 36, 6113-6116;
16. (c) Lafargue, P.; Guenot, P.; Lellouche, J. P. Preparation of 2-thiazolines from (1,2)-thioamido-alcohols; DAST as a useful reagent. Synlett. 1995, 171-172;
17. (d) Mahler, S. G.; Serra, G. L.; Antonow, D.; Manta, E. Deoxo-fluor-mediated cyclodehydration of β-hydroxy thioamides to the corresponding thiazolines. Tetrahedron Lett. 2001, 42, 8143-8146.
18. (a) Wipf, P.; Miller, C. P.; Venkataraman, S.; Fritch, P. C. Thiolysis of oxazolines: A new, selective method for the direct conversion of peptide oxazolines into thiazolines. Tetrahedron Lett. 1995, 36, 6395-6398;
19. (b) Wipf, P.; Uto, Y. Total synthesis and revision of stereochemistry of the marine metabolite trunkamide A. J. Org. Chem. 2000, 65, 1037-1049.
20. White, J. D.; Kim, T. S.; Nambu, M. Synthesis of curacin A: A powerful antimitotic from the cyanobacterium lyngbyamajuscula. J. Am. Chem. Soc. 1995, 117, 5612-5613.
21. Peiwen, Z.; Jason, E. B.; Christopher, T. B.; Nicholas, R. N. The direct synthesis of 2-oxazolines from carboxylic esters using lanthanide chloride as catalyst. Tetrahedron Lett. 1997, 38, 7019-7020.
22. Padmavathi, V.; Chandra Obula Reddy, B.; Venkata Subbaiah, D. R. C.; Padmaja, A. Sulfonyl acetic acids - source for substituted 2-oxazolines. Indian J. Chem. 2004, 43B, 2456-2458.
23. 2. J. Org. Chem. 1983, 48, 2167-2188.
24. (a) Barton, D. H. R.; Lester, D. J.; Ley, S. V. Regeneration of ketones from hydrazones, oximes, and semicarbazones by benzeneseleninic anhydride. J. Chem. Soc., Chem. Commun. 1977, 445-446;
25. (b) Bandgar, B. P.; Shaikh, S. I.; Iyer, S. Synthetic methods, 1: Oxidative deoximation with sodium perborate. Synth. Commun. 1996, 26, 1163-1168;
26. (c) Bose, D. S.; Srinivas, P. Oxidative cleavage of oximes with peroxymonosulfate ion. Synth. Commun. 1997, 27, 3835-3838.
27. (a) Curran, D. P.; Brill, J. F.; Rakiewicz, D. M. A mild reductive conversion of oximes to ketones. J. Org. Chem. 1984, 49, 1654-1656;
28. (b) Drabowicz, J. Rapid deoximation with pyridinium chlorochromate/ hydrogen peroxide system. Synthesis 1980, 125-126.
29. Laszlo, P.; Polla, E. Carbonyl regeneration from semicarbazones, tosylhydrazones, phenylhydrazones, and 2,4-dinitrophenylhydrazones by clay-supported ferric nitrate. Synthesis 1985, 439-440.
30. Aizpurua, J. M.; Palomo, C. Chlorotrimethylsilane/chromium(VI) reagents as new versatile oxidation systems. Tetrahedron Lett. 1983, 24, 4367-4370.
31. Maloney, J. R.; Lyle, R. E.; Scavedra, J. E.; Lyle, G. G. Oxidative deoximation with pyridinium chlorochromate. Synthesis 1978, 212-213.
32. Bose, S. D.; Srinivas, P. A mild and versatile method for the oxidative cleavage of oximes and tosylhydrazones to carbonyl compounds. Synlett. 1998, 977-978.
33. Rao, C. G.; Radhakrishna, A. S.; Singh, B. B.; Bhatnagar, S. P. Oxidative cleavage of oximes with triethylammonium chlorochromate. Synthesis 1983, 808-808.
34. Aizpurua, J. M.; Juaristi, M.; Lecea, B.; Palomo, C. Reagents and synthetic methods, XL: Halosilanes/chromium trioxide as efficient oxidizing reagents. Tetrahedron 1985, 41, 2903-2911.
35. de Lijser, H. J. P.; Fardoun, F. H.; Sawyer, J. R.; Quant, M. Photosensitized regeneration of carbonyl compounds from oximes. Org. Lett. 2002, 4, 2325-2328.
36. Srilakshmi, K. N.; Surendra, K.; Nageswar, Y. V. D.; Rama Rao, K. Deoximation of oximes with 2-iodylbenzoic acid in water in the presence of β-cyclodextrin. Synthesis 2003, 1968-1970.
37. Vogel, A. I. A Text Book of Practical Organic Chemistry, 5th Edn.; Longman: London, 1989.
38. Bhaskar Reddy, D.; Muralidhar Reddy, M.; Ramana Reddy, P. V. Phenacylthio/sulfonylacetates as synthons: Synthesis and conformational aspects of 1,4-thio morpholines - Part III. Indian J. Chem. 1993, 3213, 1018-1023.
39. Iraj, M. B.; Ahamad, R. K.; Seyedeh, F. H. A novel and chemoselective synthesis of 2-aryloxazolines and bis-oxazolines catalyzed by Bi(III) salts. Synlett. 2005, 18, 2747-2750.
40. Nobutaka, S.; Yasuji, I. A single-step synthesis of 2-substituted 2-thiazolines. Bull. Chem. Soc. Jpn. 1976, 49, 3155-3158.