A Novel Catechol Compound, an Unusual Side Reaction Product of a β-Ketoester with Pyruvic Aldehyde and Its Inhibition by Sodium Dithionite

Synthetic Communications

Volumn 33, Issue 22, 2003, Pages 3977-3982

  Kato, Takeaki ^a   Mochizuki, Masao ^b   Okano, Shigeru ^b   Matsuo, Noritada ^b  

^a Marchandise Development Lab   (Japan)

^b SUMITOMO CHEMICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BETA OXOCARBOXYLIC ACID ESTER; CATECHOL DERIVATIVE; ESTER DERIVATIVE; METHYLGLYOXAL; SODIUM DITHIONITE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0345276561     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120026323     Document Type: Article

References (14)

1. Schechter, M.S.; Green, N.; LaForge, F.B. Constituents of pyrethrum flowers. XXIII. Cinerolone and the synthesis of related cyclopentenolones. J. Am. Chem. Soc. 1949, 71, 3165-3173.
2. Naumann, K. Chemistry of Plant Protection 5, Synthetic Pyrethroid Isecteides; Springer-Verlag, 1990.
3. Buchi, G.; Minster, D.; Young, J.C.E. A new synthesis of rethrlones. J. Am. Chem. Soc. 1971, 93, 4319-4320; Romanet, R.F.; Schlessinger, R.H. A new and highly efficient synthesis of rethrolones. J. Am. Chem. Soc. 1974, 96, 3701-3702; Ono, N.; Tanabe, Y.; Tanikaga, R.; Kaji, A.; Matsuo, N. A new synthesis of allethrolone. Bull. Chem. Soc. Japan 1980, 53, 3033-3034.
4. Buchi, G.; Minster, D.; Young, J.C.E. A new synthesis of rethrlones. J. Am. Chem. Soc. 1971, 93, 4319-4320; Romanet, R.F.; Schlessinger, R.H. A new and highly efficient synthesis of rethrolones. J. Am. Chem. Soc. 1974, 96, 3701-3702; Ono, N.; Tanabe, Y.; Tanikaga, R.; Kaji, A.; Matsuo, N. A new synthesis of allethrolone. Bull. Chem. Soc. Japan 1980, 53, 3033-3034.
5. Buchi, G.; Minster, D.; Young, J.C.E. A new synthesis of rethrlones. J. Am. Chem. Soc. 1971, 93, 4319-4320; Romanet, R.F.; Schlessinger, R.H. A new and highly efficient synthesis of rethrolones. J. Am. Chem. Soc. 1974, 96, 3701-3702; Ono, N.; Tanabe, Y.; Tanikaga, R.; Kaji, A.; Matsuo, N. A new synthesis of allethrolone. Bull. Chem. Soc. Japan 1980, 53, 3033-3034.
6. Ellison, R.A. Methods for the synthesis of 3-oxocyclopentenes. Synthesis 1973, 397-412.
7. Scettri, A.; Piancatelli, G.; D'Auria, M.; David, G. General route and mechanism of the rearrangement of the 4-substituted 5-hydoroxy-3-oxocyclopentenes into the 2-substituted analogs. Tetrahedron 1979, 35, 135-138.
8. Gault, H.; Burkhard, J. Ketolic condensations of acetylacetic ester with formaldehyde. Compt. Rend. 1934, 199, 795-797; Chem. Abstr. 1935, 29, 1390; Gault, H.; Wenling, T. Several keto condensation products of ethyl acetoacetate and acetaldehyde. Bull. Soc. Chim. 1936, 5 (3), 53-70; Chem. Abstr. 1936, 30, 3412.
9. Gault, H.; Burkhard, J. Ketolic condensations of acetylacetic ester with formaldehyde. Compt. Rend. 1934, 199, 795-797; Chem. Abstr. 1935, 29, 1390; Gault, H.; Wenling, T. Several keto condensation products of ethyl acetoacetate and acetaldehyde. Bull. Soc. Chim. 1936, 5 (3), 53-70; Chem. Abstr. 1936, 30, 3412.
10. Gault, H.; Burkhard, J. Ketolic condensations of acetylacetic ester with formaldehyde. Compt. Rend. 1934, 199, 795-797; Chem. Abstr. 1935, 29, 1390; Gault, H.; Wenling, T. Several keto condensation products of ethyl acetoacetate and acetaldehyde. Bull. Soc. Chim. 1936, 5 (3), 53-70; Chem. Abstr. 1936, 30, 3412.
11. Gault, H.; Burkhard, J. Ketolic condensations of acetylacetic ester with formaldehyde. Compt. Rend. 1934, 199, 795-797; Chem. Abstr. 1935, 29, 1390; Gault, H.; Wenling, T. Several keto condensation products of ethyl acetoacetate and acetaldehyde. Bull. Soc. Chim. 1936, 5 (3), 53-70; Chem. Abstr. 1936, 30, 3412.
12. Kato, T.; Mochizuki, M.; Okano, S.; Yamamoto, T. Hydroxydiketones. Japanese Patent, 30-3361 1955; Chem. Abstr. 1957, 51, 16556.
13. Kato, T.; Mochizuki, M.; Okano, S.; Yamamoto, T. Hydroxydiketones. Japanese Patent, 30-3361 1955; Chem. Abstr. 1957, 51, 16556.
14. Andersen, S.H.; Das, N.B.; Jorgensen, R.D.; Kjeldsen, G.; Knudsen, J.S.; Sharma, S.C.; Torssell, K.B.G. Silyl nitronates in organic synthesis. Routes to heterocycles and cyclopentanoids. Synthesis of allethrolone and calythrone. Acylation and cyanohydroxylation of double bonds. An exploratory study. Acta Chemica Scandinavica 1982, B (36), 1.