Dieter Binder

Über den Mechanismus derDieckmann-Reaktion von 3-(Methoxycarbonylmethylthio)-propionsäuremethylester

The mechanism of theDieckmann-reaction of methyl 3-(methoxycarbonylmethylthio)-propionate (1) to methyl 4-oxotetrahydrothiophene-3-carboxylate (2) and methyl 3-oxo-tetrahydrothiophene-2-carboxylate (3) and a simple technique for the preparation of methyl 4-oxo-tetrahydrothiophene-3-carboxylate (2) free from the isomere3 are described.

Über die Synthese von 5-Phenyl-1H-thieno[3,4—e]1,4-diazepin-2(3H)-on

The synthesis of 5-phenyl-1H-thieno[3.4—e]1.4-diazepin-2(3H)-one (16), its alkylation in position 1 and the preparation of the intermediate 3-(4-aminothienyl)-phenylketone (8) are described. In addition thieno[3.4—b]pyridin-2(1H)-one (7) is described.

Über die Synthese von 7-Chlor-1,3-dihydro-thieno[3,2- e ]1,4-diazepin-2-onen

The preparation of 7-chloro-1,3-dihydro-5-phenyl-thieno-[3,2-e]-1,4-diazepin-2-one (8 a) and 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-thieno[3,2-e]1,4-diazepin-2-one (8 b) as well as the methylation in position 1 are described.

Über die Synthese von substituierten Thieno[3,4—b]chinolin-9(4H)-onen

The synthesis of in position 4 substituted thieno[3.4-b]quinoline-9(4H)-ones (6) by aromatization of 1.4-dihydrothieno[3.4-b]quinoline-9(3H)-ones (4) and attempts to cyclize 4-phenylamino-3-thiophenecarboxylic acid (3c), or derivatives thereof, to compounds of type6 are described.

Über die Synthese von 5-(o-Trifluormethylphenyl)-1H-thieno[3,4—e]-1,4-diazepin-2(3H)-onen

The synthesis of 5-(o-trifluoromethylphenyl)-1H-thieno-[3,4-e]1,4-diazepin-2(3H)-one (7) and its nitration and chlorination in pos. 8 are described.

Über die Synthese von 4,9-Dihydro-9-(2-dimethylaminoäthyl)-4-methyl-thieno[3,4-b][1,5]benzodiazepin-10-on

The synthesis of the title compound6 c, starting with the condensation of o-phenylenediamine and methyl 4-oxotetrahydrothiophene-3-carboxylate (1) to 1.3.4.9-tetrahydrothieno[3.4-b] [1.5]benzodiazepin-10-one (2), is described.The structures of other products of this condensation, 1.3-dihydro-1-[3-(2.5-dihydrothienyl)]-benzimidazol-2-one (3) and 1.3-dihydro-1-[3-(2.3-dihydrothienyl)]-benzimidazol-2-one (4), are confirmed by their1H-NMR-spectra and by the1H-NMR-spectra of their desulfurization products.

ber die Synthese von 5-(o-Chlorphenyl)-7-trifluormethyl-1Hthieno[3,2?e]-1,4-diazepin-2(3H)-on@@@5-(o-chlorophenyl)-7-trifluoromethyl-1H-thieno[3.2?e]-1.4-diazepin-2(3H)-one

The synthesis of 5-(o-chlorophenyl)-7-trifluoromethyl-1H-thieno[3.2−e]-1.4-diazepin-2(3H)-one (10) starting from ethyl 3-amino-5-trifluoromethyl-2-thiophenecarboxylate (1) is described.The synthesis of 5-(o-chlorophenyl)-7-trifluoromethyl-1H-thieno[3.2−e]-1.4-diazepin-2(3H)-one (10) starting from ethyl 3-amino-5-trifluoromethyl-2-thiophenecarboxylate (1) is described.

Über die Synthese von Amino-trifluormethyl-thiophencarbonsäureäthylestern

The syntheses of ethyl 4-amino-2-trifluormethyl-thiophene-3-carboxylate (14) and of ethyl 3-amino-5-trifluormethylthiophene-2-carboxylate (15) are described.The structures of14 and15 are confirmed by NMR-spectroscopy. TheDieckmann reaction of the important intermediate ethyl 3-(carbethoxymethylthio)-3-trifluormethyl-propionate is described.

Über die Synthese von 8-Chlor- und 7,8-Dichlor-5-phenyl-1H-thieno[3,2-e]1,4-diazepin-2(3H)-on

The preparation of the title compounds (13 and14) and there methylation in position 1 are described.

Über Synthese und Strukturbeweis von substituierten 5-Phenyl-1H-thieno[3,4—e]1,4-diazepin-2(3H)-onen

Chlorination and nitration of 5-phenyl-1H-thieno-[3.4-e]1.4-diazepin-2(3H)-one (1) are described. It is proved by unambiguous synthesis of the chloro derivative that electrophilic substitution of1 occurs in position 8. Chlorinated1 is methylated in position 1.Chlorination and nitration of 5-phenyl-1H-thieno-[3.4-e]1.4-diazepin-2(3H)-one (1) are described. It is proved by unambiguous synthesis of the chloro derivative that electrophilic substitution of1 occurs in position 8. Chlorinated1 is methylated in position 1.