Scandium triflate catalyzed formation of benzothiazole from 2- aminobenzenethiol and formaldehyde in the presence of water

Heterocycles

Volumn 52, Issue 3, 2000, Pages 1037-1040

  Itoh, Takashi ^a   Nagata, Kazuhiro ^a   Miyazaki, Michiko ^a   Ohsawa, Akio ^a  

^a SHOWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 BENZOQUINONE DERIVATIVE; BENZOTHIAZOLE; IMINE; OXYGEN; SCANDIUM; THIOPHENOL DERIVATIVE;

AROMATIZATION; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0034162740     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-99-s125     Document Type: Article

References (12)

1. This paper is dedicated to the Professor Teruaki Mukaiyama on the occasion of his 73rd birthday.
2. "Lanthanides:Chemistry and Use in Organic Synthesis," ed. by S. Kobayashi, Springer, Berlin, 1999.
3. S. Kobayashi, "Organic Synthesis in Water," ed. by P. A. Grieco, Blackie Academic & Professional, London, 1998, pp 262-305.
4. a) J. H. Forsberg, V. T. Spaziano, T. M. Balasubramanian, G. K. Liu, S. A. Kinsley, C. A. Duckworth, J. J. Poteruca, P. S. Brown, and J. L. Millwe, J. Org. Chem., 1987, 52, 1017.
5. b) S. Matsubara, M. Yoshioka, and K. Utimoto, Chem. Lett., 1994, 827.
6. M. Meguro, N. Asao, and Y. Yamamoto, Tetrahedron Lett., 1994, 35, 7395.
7. Any current textbooks of heterocycles include the synthesis via this process; see, a) T. L. Gilchrist, "Heterocyclic Chemistry, " 3rd ed. Longman, Harlow, 1997.
8. b) J. A. Joule, K. Mills, and G. F. Smith, "Heterocyclic Chemistry," 3rd ed. Chapman & Hall, London, 1995.
9. Pioneering works of this field were presented recently in a review; see, S. Kobayashi and H. Ishitani, Chem. Rev., 1999, 99, 1069.
10. There are few reports concerning the synthesis of parent benzothiazole from 2-aminobenzenethiol and formaldehyde (or its derivative). A paper showed that 2-aminobenzenethiol, ethyl orthoformate, and sulfuric acid were reacted without a solvent at 170-180°C to give 2 in 75-85%; G. L. Jenkins, A. M. Knevel, and C. S. Davis, J. Org. Chem., 1961, 26, 274.
11. Even when 4 mmol of the substrate was used under the same conditions, the reaction proceeded smoothly. Thus, we think that the procedure is of practical use.
12. 3, the yield of 2 was remained at 10% (in the absence of an acid: 12% (Table 1, Entry 1).