Process for the production of thiophenes from alpha-methylene ke

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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549 43, C07D33350

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048763616

ABSTRACT:
Described is a novel process which can be carried out as a single-stage synthesis for the production of substituted and/or b,d- ortho-fused thiophenes. Serving as starting compounds and .alpha.-methylene ketones which are reacted in an preferably alcoholic solvent with bromine whereafter the formed intermediate product after separation from the solvent is reacted directly with a sulphurising agent. Preferably under reflux conditions in a suitable solvent to form the end product.
In this way also hitherto unknown ortho-fused thiophene compounds are synthesized more especially those with 5 or 9 rings condensed with one another.

REFERENCES:
patent: 4219657 (1980-08-01), Berger et al.
Claus-Detlef Czogalla et al., "Schwefelverbindungen Des Erdols XI Eine Eintopfsynthese Fur 2,5-Diphenylthiophene Und b,d-Anellierte Thiophene Aus Methylenketonen", Phosphorus and Sulfur, vol. 35, pp. 127-131 (1988).
H. D. Hartough et al., Compounds with Condensed Thiophene Rings, Interscience Publishers, Inc., N.Y., title page (1954).
Chemical Abstracts, vol. 99, p. 534, Abstract 139146q (1983).
F. Boberg et al., Liebigs Annalen Der Chemie, Nr. 9, pp. 1598-1607 (1983).
Claus-Detlef Czogalla et al., Sulfur Reports, "Sulfur Compounds in Fossil Fuels I", vol. 3, pp. 121-170, Jul. 1983.
John Ashby et al., Advanced Heterocycl. Chem., "Recent Advances in the Chemistry of Dibenzothiophenes", vol. 16, pp. 214-217 (1974).
Scholz et al., Z. Chem., 7. Jg. (1967), Helt 9, p. 351.

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