A Facile Synthesis of Derivatives of (1,3,4-Thiadiazol-2-yl)glycine and Its Phosphonyl Analogue

Synthesis

Volumn , Issue 18, 2003, Pages 2851-2857

  Golovchenko, Aleksandr V ^a   Pilyo, Stepan G ^a   Brovarets, Vladimir S ^a   Chernega, Alexander N ^b   Drach, Boris S ^a  

^a INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Ukraine)

Author keywords

(1,3,4 thiadiazol 2 yl)glycine; 1,3 oxazoles; 2,2,2 trichloroethylphosphonates; 3,3 dichloroacrylates; Aryl isothiocyanates; aminoalkylphosphonic acids; aminocarboxylic acids

Indexed keywords

DERIVATIVES; HEATING; SYNTHESIS (CHEMICAL);

ADDUCTS;

AROMATIC COMPOUNDS;

(1,3,4 THIADIAZOL 2 YL)GLYCINE; 2 (4 METHYLBENZOYLAMINO)METHYL 5 (4 TOLUIDINO) 1,3,4 THIADIAZOLE; 5 ANILINO 2 (BENZOYLAMINO)METHYL 1,3,4 THIADIAZOLE; ACETIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; DIETHYL 5 HYDRAZINO 2 PHENYL 1,3 OXAZOL 4 YLPHOSPHONATE; DIETHYL 5 HYDRAZINO 2 STYRYL 1,3 OXAZOL 4 YLPHOSPHONATE; DIMETHYL 5 (ANILINO 1,3,4 THIADIAZOL 2 YL)(4 METHYLBENZOYLAMINO)METHYLPHOSPHONATE; DIMETHYL 5 (ANILINO 1,3,4 THIADIAZOL 2 YL)(BENZOYLAMINO)METHYLPHOSPHONATE; DIMETHYL 5 (ANILINO 1,3,4 THIADIAZOL 2 YL)(CINNAMOYLAMINO)METHYLPHOSPHONATE; DIMETHYL 5 HYDRAZINO 2 (4 METHYLPHENYL 1,3 OXAZOL 4 YLPHOSPHONATE; DIMETHYL 5 HYDRAZINO 2 PHENYL 1,3 OXAZOL 4 YLPHOSPHONATE; DIMETHYL 5 HYDRAZINO 2 STYRYL 1,3 OXAZOL 4 YLPHOSPHONATE; ETHYL 5 ANILINO 1,3,4 THIADIAZOL 2 YL(BENZOYLAMINO)ACETATE; ETHYL 5 HYDRAZINO 2 PHENYL 1,3 OXAZOLE 4 CARBOXYLATE; ETHYLBENZOYLAMINO[5 (4 TOLUIDINO) 1,3,4 THIADIAZOL 2 YL]ACETATE; GLYCINE DERIVATIVE; METHYL 2 PHENYL 5 (4 PHENYLTHIOSEMICARBAZIDO) 1,3 OXAZOLE 4 CARBOXYLATE; METHYL 4 METHYLBENZOYLAMINO[5 (4 METHOXYANILINO) 1,3,4 THIADIAZOL 2 YL]ACETATE; METHYL 4 METHYLBENZOYLAMINO[5 (4 TOLUIDINO) 1,3,4 THIADIAZOL 2 YL]ACETATE; METHYL 5 ANILINO 1,3,4 THIADIAZOL 2 YL(4 METHYLBENZOYLAMINO)ACETATE; METHYL 5 ANILINO 1,3,4 THIADIAZOL 2 YL(BENZOYLAMINO)ACETATE; METHYL 5 HYDRAZINO 2 (4 METHYLPHENYL) 1,3 OXAZOLE 4 CARBOXYLATE; METHYL 5 HYDRAZINO 2 PHENYL 1,3 OXAZOLE 4 CARBOXYLATE; METHYL 5 [(4 METHYLPHENYL)THIOSEMICARBIZIDO] 2 PHENYL 1,3 OXAZOLE 4 CARBOXYLATE; METHYLBENZOYLAMINO[5 (4 METHOXYANILINO) 1,3,4 THIADIAZOL 2 YL]ACETATE; METHYLBENZOYLAMINO[5 (4 TOLUIDINO) 1,3,4 THIADIAZOL 2 YL]ACETATE; PHOSPHONIC ACID DERIVATIVE; THIADIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; HEAT TREATMENT; SUBSTITUTION REACTION; SYNTHESIS; X RAY ANALYSIS;

EID: 0347950979     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-42458     Document Type: Article

References (28)

1. Adlington, R. M.; Baldwin, J. E.; Catteric, D.; Pritchard, G. J. J. Chem. Soc., Perkin Trans, 1 1999, 855.
2. Adlington, R. M.; Baldwin, J. E.; Catteric, D.; Pritchard, G. J. J. Chem. Soc., Perkin Trans, 1 2000, 299.
3. Jones, R. C. F.; Berthelot, D. J. C.; Iley, J. N. Chem. Commun. 2000, 2131.
4. Adlington, R. M.; Baldwin, J. E.; Catteric, D.; Pritchard, G. J.; Tang, L. T. J. Chem. Soc., Perkin Trans, 1 2000, 2311.
5. Adlington, R. M.; Baldwin, J. E.; Catteric, D.; Pritchard, G. J. J. Chem. Soc., Perkin Trans, 1 2001, 668.
6. Stensbol, T. B.; Uhlmann, P.; Morel, S.; Eriksen, B. L.; Felding, J.; Kromann, H.; Hermit, M. B.; Greenwood, T. R.; Bräuner-Osborne, H.; Madsen, U.; Junager, F.; Krogsgaard-Larsen, P.; Begtrup, M.; Vedso, P. J. Med. Chem. 2002, 45, 19.
7. Myers, A. G.; Gleason, J. L. J. Org. Chem. 1996, 61, 813.
8. Whitlock, B. J.; Lipton, S. H.; Strong, F. M. J. Org. Chem. 1965, 30, 115.
9. Eugster, H.; Müller, G. F. R.; Good, R. Tetrahedron Lett. 1965, 1813.
10. Matzen, L.; Engesgaard, A.; Ebert, B.; Didriksen, M.; Frolund, B.; Krogsgaard-Larsen, P.; Jaroszewski, J. W. J. Med. Chem. 1997, 40, 520.
11. (a) Lunn, W. H. W.; Schoepp, D. D.; Lodge, D.; True, R. A.; Millar, J. D. Book of Abstracts, 12th International Symposium on Medicinal Chemistry, Basel, Switzerland, September 13-17, 1992; Swiss Chemical Society: Basel, 1992, P-041.
12. (b) Lunn, W. H. W.; Schoepp, D. D.; Lodge, D.; True, R. A.; Millar, J. D. Book of Abstracts, 12th International Symposium on Medicinal Chemistry, Basel, Switzerland, September 13-17, 1992; Swiss Chemical Society: Basel, 1992, A-040.
13. Drach, B. S.; Miskevich, G. N. Zh. Org. Khim. 1974, 10, 2315; Chem. Abstr. 1975, 82, 72843.
14. Drach, B. S.; Miskevich, G. N. Zh. Org. Khim. 1974, 10, 2315; Chem. Abstr. 1975, 82, 72843.
15. Matsumura, K.; Saraie, T.; Hashimoto, N. Chem. Pharm. Bull 1976, 24, 924.
16. Pilyo, S. G.; Brovarets, V. S.; Vinogradova, T. K.; Chernega, A. N.; Drach, B. S. Zh. Obshch. Khim. 2001, 71, 310.
17. Boulton, A. J.; Katritzky, A. R.; Hamid, A. M. J. Chem. Soc. C 1967, 2005.
18. Brovarets, V. S.; Vydzhak, R. N.; Pilyo, S. G.; Zyuz, K. V.; Drach, B. S. Zh. Obshch. Khim. 2001, 71, 1822.
19. Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity; Kukhar, V. P.; Hudson, H. R., Eds.; Wiley: Chichester, 2000.
20. Boduszek, B. Phosphorus, Sulfur Silicon Relat. Elem. 1995, 104, 63.
21. Boduszek, B. Phosphorus, Sulfur Silicon Relat. Elem. 1996, 113, 209.
22. Boduszek, B. Tetrahedron 1996, 52, 12483.
23. Cottier, L.; Descotes, G.; Gonera, G.; Grabowski, G.; Levkowski, J.; Skowronski, R. Phosphorus, Sulfur Silicon Relat. Elem. 1996, 118, 181.
24. Journet, M.; Cai, D.; Larson, R. D.; Reider, P. J. Tetrahedron Lett. 1998, 39, 1717.
25. North, A. C. T.; Phillips, D. C.; Mathews, F. S. Acta Crystallogr., Sect. A 1968, 24, 351.
26. Watkin, D. J.; Prout, C. K.; Carruthers, J. R.; Betteridge, P. W. CRYSTALS, Issue 10; Chemical Crystallography Laboratory, University of Oxford: Oxford, 1996.
27. Carruthers, J. R.; Watkin, D. J. Acta Crystallogr., Sect. A 1979, 35, 698.
28. Full crystallographic details have been deposited at Cambridge Crystallographic Data Centre (CCDC). Any request to the CCDC for this material, should quote the full literature citation and reference number CCDC 215589.