[5,5] sigmatropic shift of N-phenyl-N'-(2-thiazolyl)hydrazines and N,N'- bis(2-thiazolyl)hydrazines into 2-amino-5-(p-aminophenyl)thiazoles and 5,5'- bis(2-aminothiazole) derivatives

Tetrahedron Letters

Volumn 41, Issue 20, 2000, Pages 3883-3886

  Lee, Boong Won ^a   Lee, Seung Dal ^a  

^a Korea Military Academy   (South Korea)

Author keywords

Acid catalyst; Benzidine type rearrangement; Hydrazine; Thiazole; Thiourea

Indexed keywords

HYDRAZINE DERIVATIVE; THIAZOLE DERIVATIVE; THIOUREA DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; POLYMERIZATION; REACTION ANALYSIS;

EID: 0012268729     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00493-7     Document Type: Article

References (12)

1. (a) Shine, H. J. In Aromatic Rearrangement; Elsevier: New York, 1967; pp. 126-179.
2. (b) Shine, H. J. In Mechanism of Molecular Migration; Thyagarajan, B. S., Ed.; Interscience: New York, 1969; Vol. 2, pp. 191-247.
3. (c) Dewar, M. J. S. In Molecular Rearrangements; de Mayo, P., Ed.; Interscience: New York, 1969; Vol. 1, pp. 323-343.
4. (d) Cox, R. A.; Buncel, E. In The Chemistry of the Hydrazo, Azo and Azoxy Groups; Patai, S., Ed.; Wiley: New York, 1975; pp. 775-859.
5. (e) Banthrope, D. V. Chem. Rev. 1970, 70, 295-322.
6. (f) Olah, G. A.; Dunne, K.; Kelly, D. P.; Mo, Y. K. J. Am. Chem. Soc. 1972, 94, 7438-7447.
7. (g) Bunton, C. A.; Rubin, R. J. J. Am. Chem. Soc. 1976, 98, 4236-4246.
8. (h) Park, K. H.; Kang, J. S. J. Org. Chem. 1997, 62, 3794-3795.
9. 6) δ: 180. (d) Compound 2b is also commercially available from Aldrich Chem. Co.
10. (a) Hantzsch, A.; Wever, J. H. Ber. 1887, 20, 3118-3128.
11. (b) Hantzsch, A.; Traumann, V. Ber. 1888, 21, 938-946.
12. 6) δ: 102.5, 146.5, 168.