Teikoku Chemical Industry Co., Ltd.

Seiichi Kitamura

Masanao Matsui

Kazumasa Ohba

Takeshi Kitahara

Masahiro Morioka

Kenji Mori

Ureylenethiophanes and their related compounds of the formula: ##SPC1## Having a cis-configuration on the ureylene or thioureylene juncture, which are useful as the intermediates in the synthesis of biologically active biotin and its related compounds, can be produced selectively by reacting the corresponding compounds of the formula: ##SPC2## With isocyanates or isothiocyanates wherein R is a hydrogen atom, an alkyl group or an aralkyl group, R.sub.1 and R.sub.2 are each a hydrogen atom or an aliphatic hydrocarbon group bearing or not a carboxyl group or any other group convertible thereto at the terminal position, X is a halogen atom, Y is an oxygen atom or a sulfur atom and Z is an oxygen atom, a sulfur atom, a sulfinyl group or a sulfonyl group.

Ureylenethiophanes and their related compounds, and production thereof

Polyene compounds of the formula: ##EQU1## wherein R' is protected or unprotected hydroxyl or a group of the formula: ##EQU2## (in which R' and R'' are each carboxyl or a group convertible into carboxyl on hydrolysis), m is a positive integer and n is 0 or a positive integer, which are useful as intermediates in the synthesis of coenzyme Q, can be produced advantageously through a step for the dehydration of a compound of the formula: ##EQU3## wherein R', m and n are each as defined above.

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Ibaraki, Japan

Seiichi Kitamura