[Study of 1,5-benzodiazepines. II. Synthesis of 2,4-di-(N-alkyl,N-phenyl)amino-3H-1,5-benzodiazepine].

Following the procedure we described for synthesizing analogous compounds in Note I (7), reaction of N,N-dialkyl or (N-alkyl,N-phenyl)ethoxycarbonylacetamides with 4-chloro-1,2-phenylendiamine, in the presence of phosphorus oxychloride, afforded 2,3-dihydro-2-oxo-4-dialkyl (N-alkyl,N-phenyl)amino-chloro-1H-1,5-benzodiazepines. When a large amount of phosphorus oxychloride was employed in the reaction, the formation of 2,4-di-(N-alkyl,N-phenyl)amino-3H-1,5-benzodiazepines was achieved, starting from suitable o-phenylendiamines and (N-alkyl,N-phenyl)ethoxycarbonylacetamides

[Studies on 1,5-benzodiazepine. I. Derivatives of 4-amino-1,5-benzodiazepine].

Condensation of o-phenylendiamine and N,N-dialkyl-ethoxycarbonylacetamides in the presence of phosphorus oxychloride afforded 2,3-dihydro-2-oxo-4-dialkylamino-1H-1,5-benzodiazepines. These same compounds with a substituent in the 3 position were obtained when N,N-dialkylamino-alpha-ethoxycarbonyl-alpha-alkylacetamides were employed in the reaction. In a similar manner from N-phenyl-o-phenylendiamine the synthesis of 1-phenyl-2,3-dihydro-2-oxo-4-dialkylamino-1H-1,5-benzodiazepines was achieved. The formation of benzimidazole-2-acetic acid derivatives was observed in these reactions

[Chemical and pharmacological research on pyran derivatives. VI. 2-Dialkylamino-4-oxo-4H-naphto/1,2-b/pyrans and derivatives].

Aminonaphthopyranones I (NRR1 = NMe2, NMeEt, NEt2, pyrrolidino, piperidino, R2-R4 = H; NRR1 = NMe2, R2 = Me, OMe, R3 = R4 = H; NRR1 = NMe2, R2 = R4 = H, R3 = NMe2, NEt2) were prepd. by condensing 1-naphthols with RR1NCOCH2CO2Et. Some I were aminomethylated to I (NRR1 = NMe2, NMeEt, NEt2, R2 = R3 = H, R4 = morpholino, piperidino, 4-methylpiperazino). I (R4 = H) showed some anticonvulsant activity

[1,5-Benzodiazepines. III. Synthesis of 2,4-bisdialkylamino-3H-1,5-benzodiazepines].

Benzodiazepines I (NRR1 = NMe2, NEt2, pyrrolidino; R2 = SMe) were prepd. by thiolating benzodiazepinones and methylating the thiones. I (R2 = SMe) were aminated to give I (R2 = NMe2, pyrrolidino, piperidino, morpholino). I (R2 = SMe) were central nervous system depressants and anticonvulsants, whereas I (R2 = amino) were central nervous system stimulants and convulsants