An unexpected formation of 2-aryl-3-benzyl-1,3-thiazolidin-4-ones

Synthesis

Volumn , Issue 20, 2006, Pages 3405-3408

  Cunico, Wilson ^a   Capri, Liliane R ^a   Gomes, Claudia R B ^a   Sizilio, Rosangela H ^a   Wardell, Solange M S V ^a  

^a INSTITUTO OSWALDO CRUZ   (Brazil)

Author keywords

Cyclocondensation; Thiazolidinones; Valine

Indexed keywords

ALDEHYDES; AMINO ACIDS; CHARACTERIZATION; CONDENSATION; NUCLEAR MAGNETIC RESONANCE; REACTION KINETICS; X RAY CRYSTALLOGRAPHY;

CYCLOCONDENSATION; MERCAPTOACETIC ACID; THIAZOLIDINONES; VALINE;

KETONES;

2 ARYL 2 BENZYL 1,3 THIAZOLIDIN 4 ONES; ALDEHYDE DERIVATIVE; ARENEALDEHYDE; THIAZOLIDINE DERIVATIVE; THIOGLYCOLIC ACID; UNCLASSIFIED DRUG; VALINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 33750588298     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-950213     Document Type: Article

References (15)

1. Singh, S. P.; Parmar, S. S.; Raman, K.; Stenberg, V. I. Chem. Rev. 1981, 81, 175.
2. Brickner, S. J.; Hutchinson, D. K.; Barbachyn, M. R.; Manninen, M. N.; Ulanowicz, D. A.; Garmon, S. A.; Grega, K. C.; Hendges, S. K.; Troops, D. S.; Ford, C. W.; Zurenko, G. E. J. Med. Chem. 1996, 39, 673.
3. de Souza, M. V. N. Recent Patents on Anti-Infective Drug Discovery 2006, 1, 33.
4. (a) Barreca, M. L.; Balzarini, J.; Chimirri, A.; De Clercq, E.; De Luca, L.; Holtje, H. D.; Holtje, M.; Monforte, A. M.; Monforte, P.; Pannecouque, C.; Rao, A.; Zapallà, M. J. Med. Chem. 2002, 45, 5410.
5. (b) Rao, A.; Balzarini, J.; Carbone, A.; Chimirri, A.; De Clercq, E.; Monforte, A. M.; Monforte, P.; Pannecouque, C.; Zapallà, M. Farmaco 2004, 59, 33.
6. (c) Rao, A.; Balzarini, J.; Carbone, A.; Chimirri, A.; De Clercq, E.; Monforte, A. M.; Monforte, P.; Pannecouque, C.; Zapallà, M. Antivir. Res. 2004, 63, 79.
7. (d) Rawal, R. K.; Prabhakar, Y. S.; Katti, S. B.; De Clercq, E. Bioorg. Med. Chem. 2005, 13, 6771.
8. Barreca, M. L.; Carotti, A.; Carrieri, A.; Chimirri, A.; Monforte, A. M.; Pellegrini Calace, M. L.; Rao, A. Bioorg. Med. Chem. 1997, 7, 2283.
9. Srivastava, T.; Haq, W.; Katti, S. B. Tetrahedron 2002, 58, 7619.
10. Homes, C. P.; Chinn, J. P.; Look, C. G.; Gordon, E. M.; Gallop, M. A. J. Org. Chem. 1995, 60, 7328.
11. Gudurudu, V.; Nguyen, V.; Dalton, J. T.; Miller, D. D. Synlett 2004, 2357.
12. Troutman, H. D.; Long, L. M. J. Am. Chem. Soc. 1948, 70, 3436.
13. Satsumabayashi, S.; Irioka, S.; Kudo, H.; Tsujimoto, K.; Motoki, S. Bull. Chem. Soc. Jpn. 1972, 45, 913.
14. 3): δ = 171.7 (C=O), 148.4, 138.8, 132.3, 130.1, 124.7, 121.6 (Ph), 80.6 (C2), 32.7 (C4); CG-MS: m/z (%) = 225 (10) [M], 152 (100), 105 (20), 74 (70), 51 (25).
15. -1; Theta range for data collection 1.52° to 27.45°; Reflections collected 15114; Independent reflections 3128 [R(int) = 0.0340]; Refinement method Full-matrix least-squares on F2; R1 = 0.0680, wR2 = 0.1729 [I>2σI]. Structure solution and refinement were achieved using SHELX97 and SHELXL97 (Sheldrick, G. M. SHELXS91 and SHELXL97, University of Göttingen, Germany, 1997).