Anders Hallberg

A New Synthesis of 1-Chlorophenothiazine

Abstract Derivatives of 1-chlorophenothiazine, possessing different basic side chains on the nitrogen atom, have attracted the attention of medicinal chemists in the past.1–5 Our interest in the title compound 1 stems from reports that 1-chloropromazine 25 and the corresponding trans-2-(l-chloro- lo-phenothiazinyl)-N,N-dimethylcyclopropane methylamine derivative (314 exhibit antidepressant (but not antipsychotic activity) in experimental animals. A literature survey revealed that multistep syntheses were required for the preparation of I-chlorophenothiazine (1)6-9. It has however been obtained in a single step procedure by heating a complex of phenothiazine with cupric chloride, but the yield was very low, 1.5%10.

An intramolecular anionic fries rearrangement of N-acylphenothiazines

Abstract Certain 2-substituted N-acylphenothiazines undergo a rapid intramol≐cular N→C migration on reaction with lithium N,N-dialkylamides at −78°. Preliminary studies of the scope and mechanism of this anionic version of the Fries rearrangement are reported.

TOTAL ASSIGNMENT OF THE PROTON NMR SPECTRA OF 5H‐INDOLO(1,7‐AB)(1)BENZAZEPINE, 6,7‐DIHYDRO‐5H‐INDOLO(1,7‐AB)(1)BENZAZEPINE AND PYRROLO(3,2,1‐KL)PHENOTHIAZINE

The total assignment of the 1H nmr spectrum of the three tetracyclic compounds: 5H -indolo[1,7-ab][1]benzazepine,6,7-dihydro-5H -indolo[1,7-ab ][1]benzazepine and pyrrolo[3,2,1-kl ]phenothiazine is described. Assignments were based on decoupling experiments and the spectrum of 1,10-dideuteriopyrrolo[3,2,1-kl]phenothiazine and the spectral parameters were verified by spin-simulation techniques. A temperature study of 6,7-dihydro-5H -indolo[1,7-ab][1]benzazepine was also performed.