Sumitomo Chemical Company, Limited

Shinji Nishii

Masashi Komatsu

Hiroshi Ueda

Gohfu Suzukamo

Yukio Yoneyoshi

Yoji Sakito

Naoto Konya

Shigeo Wake

Hiroko Sakane

Sachiko Takeuchi

Sachiko Asada

Takeshi Ogawa

A process for producing 1-substituted tetrahydroquinazolines represented by the formula (III): ##STR1## wherein Z represents a methylene group which is optionally substituted by an alkyl group; R.sub.6 represents an alkyl group or an aralkyl group; R.sub.1 and R.sub.2 independently represent a hydrogen atom, a halogen atom, a nitro group, an azido group, an alkyl group, an alkenyl group, an aralkyl group, an alkoxy group, an alkoxycarbonyl group, an acyloxygroup, or an amino group represented by XNR.sub.4 R.sub.5 in which X represents a direct bond, an alkylene group or a carbonyl group, and N, R.sub.4 and R.sub.5 may form together a five- or six-membered heterocyclic ring or R.sub.4 and R.sub.5 independently represent an alkyl group or an acyloxy alkyl group; and R.sub.3 represents a hydrogen atom, a halogen atom, a nitro group, an azido group, an alkyl group, an alkenyl group, an aralkyl group,an alkoxy group, or an alkoxycarbonyl group which comprises reacting tetrahydroquinazolines represented by the formula (I): ##STR2## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above with hexamethyldisilazane; and reacting the resultant product with a chloroalkanoate represented by the formula (II):

Process for producing 1-substituted tetrahydroquinazolines

A process for producing isatoic anhydrides of the formula (II): ##STR1## which comprises reacting an anthranilic acid of formula (I): ##STR2## or a salt thereof with phosgene using a mixed solvent of water and an organic solvent miscible with water and inert to the reaction;

Process for producing isatoic anhydrides

A process for producing isatoic anhydrides of the formula (II): ##STR1## which comprises reacting an anthranilic acid of formula (I): ##STR2## or a salt thereof with phosgene using a mixed solvent of water and an organic solvent miscible with water and inert to the reaction; conducting the reaction in the coexistence of an alkylpyridinium salt in an aqueous solvent; or using a mixed solvent of water and a specific amount of an organic solvent substantially immiscible with water and inert to the reaction.

A process for producing an dioxoquinazoline of following formula (II): ##STR1## wherein R.sub.1 and R.sub.2 independently represent a hydrogen atom, a halogen atom, a nitro group, a lower alkyl group, an aralkyl group, an alkoxy group, an alkoxylcarbonyl group or a group represented by YNR.sub.3 R.sub.4, wherein Y represents a direct bond, a lower alkylene group or a carbonyl group, and R.sub.3 and R.sub.4 independently represent a lower alkyl group or N, R.sub.3 and R.sub.4 may bond together to form a five- or six-membered heterocycle which comprises reacting an anthranylamide of formula (I): ##STR2## wherein X, R.sub.1 and R.sub.2 are as defined above.

Process for producing dioxoquinazolines

A process for producing 1-substituted tetrahydroquinazolines represented by the formula (III): ##STR1## as defined herein which comprises reacting tetrahydroquinazolines represented by the formula (I): ##STR2## with hexamethyldisilazane; and reacting the resultant product with a chloroalkanoate represented by the formula (II):

The object of the present invention is to provide a process for producing 1,4-dicyano-2-butene in a high yield and in an industrially advantageous way. The present invention relates to a process for producing 1,4-dicyano-2-butene which comprises reacting a butene derivative represented by the formula [1]

Process for producing 1,4-dicyano-2-butene

Disclosed is a process for producing an optically active amine represented by the formula (IV) ##STR1## wherein R.sub.7 and R.sub.8 each denote an alkyl group, aryl group or aralkyl group, providing that they do not denote the same group at the same time, and * indicates an asymmetric carbon atom, which comprises reacting an asymmetric reducing agent obtained from (1) an optically active amine derivative represented by the formula (I) ##STR2## wherein R.sub.1 denotes an alkyl group, aryl group or aralkyl group; R.sub.2 denotes a hydrogen atom, alkyl group or aralkyl group; R.sub.3 denotes an aryl group or a substituent represented by the formula (II) ##STR3## wherein R.sub.4 and R.sub.5 each denote a hydrogen atom, aryl group or aralkyl group, and * is as defined above, (2) a metal borohydride and (3) sulfuric acid, with either the syn-isomer or the anti-isomer of an oxime derivative represented by the formula (III) or with a mixture rich in either one of the two isomers ##STR4## wherein R.sub.6 denotes an alkyl group, aralkyl group or alkyl-substituted silyl group, and R.sub.7 and R.sub.8 are as defined above. The optically active amine obtained can be used as a resolving agent for preparing medicinal agents, agricultural chemicals, or intermediates thereof.

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Osaka, Japan

Shinji Nishii