Summary
2,3-Dihydro-3-oxo-benzo[b]thiophen-1,1-dioxide (1) reacts as CH-acidic component with amidines of orthoesters and anilines resp. to give the anilinomethylene derivates3, 4, and5. With triethyl orthoformiate the hydroxymethylene-compound7 is obtained. Anilino- and phenylhydrazino derivates8 and9 prove the carbonyl activity of1, azo-coupling leads to10, whereas treatment of1 with sulfur and malononitrile yields the benzo[b]thieno[2,3-d]thiophenes11. Introduction of substituents with active NH-functions in position 2 of the dicyanomethylene-product2, such as azocoupling, reaction with phenyl isocyanate and formation of enamines, leads to ring closure reactions between a nitrile and the NH-group. Thereby the phenyl-benzo[4,5]thieno[2,3-c]pyridazines12, the phenyl-1H-benzo[4,5]thieno[2,3-c]pyridines13 and the phenylamino-benzo[4,5]thieno[2,3-c]pyridines14 are obtained.13C and15N-NMR spectroscopy was used as proof of the ring closure reactions.
Similar content being viewed by others
Literatur
85. Mitt.: Dworczak R., Sterk H., Junek H. (1990) Monatsh. Chem. (im Druck)
Feist F. (1925) Chem. Ber.58: 2311
Regitz M. (1965) Chem. Ber.98: 36
Matsakanova M., Vanags G. Y. (1960) Doklady Akad. Nauk SSSR132: 615; Chem. Abstr.54 (1960) 24636
Sandoz A. G., Basel, UK Patent: 2 026 528; Chem. Abstr.93 (1980) 48 539 und Franz. Pat. 2 438 045 (1980); Chem. Abstr.94 (1981) 4953
Shenoy V. U., Patel V. P., Seshadri S. (1989) Dyes Pigments11: 37; Bello K. A., Griffiths J. (1986) J. Chem. Soc. Chem. Commun.: 1639
Junek H., Klade M., Sterk H (1989) Monatsh. Chem.120: 781
Wolfbeis O. S. (1981) Chem. Ber.114: 3471
Uray G., Wolfbeis O. S. (1981) Monatsh. Chem.112: 627
Kadin S. B. (1969) J. Org. Chem.34: 3178
Martin G. J., Martin M. L., Gouesward J. P. (1981)15N-NMR Spectroscopy. Springer, Berlin Heidelberg New York
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Tauber, C., Klade, M., Sterk, H. et al. Ein Beitrag zur Chemie des 2,3-Dihydro-3-oxo-benzo[b]thiophen-1,1-dioxids Synthesen mit Nitrilen, 86. Mitt.. Monatsh Chem 121, 299–309 (1990). https://doi.org/10.1007/BF00808932
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00808932