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Synthetic Communications | 1983

A New Synthesis of 1-Chlorophenothiazine

Anders Hallberg; Arnold R. Martin

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.


Tetrahedron Letters | 1986

An intramolecular anionic fries rearrangement of N-acylphenothiazines

Anders Hallberg; Arne Svensson; Arnold R. Martin

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.


Journal of Heterocyclic Chemistry | 1983

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

Anders Hallberg; Torsten Dahlgren; Arnold R. Martin; Kenner Christiansen

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.


Journal of Heterocyclic Chemistry | 1982

Acylations of 1,10‐dilithiophenothiazine. A new synthesis of 1‐formylphenothiazine

Anders Hallberg; Arnold R. Martin


Journal of Heterocyclic Chemistry | 1984

Mass spectral fragmentation patterns of heterocycles. VI. Carbazole and 1,8‐dideuteriocarbazole

Anders Hallberg; Arnold R. Martin


Journal of Heterocyclic Chemistry | 1984

The assignment of the 1H-NMR and 13C-NMR spectra of 5H-dibenz[b,f]azepine and 10,11-dihydro-5H-dibenz[b,f]azepine

Anders Hallberg; Ibrahim Al-Showaier; Arnold R. Martin


Journal of Heterocyclic Chemistry | 1983

On the assignment of the 13C-NMR spectrum of phenothiazine

Anders Hallberg; Ibrahim Al-Showaier; Arnold R. Martin


Journal of Heterocyclic Chemistry | 1985

Preparation of pyrrolo[3,2,1-jk]carbazole by nickel(0) mediated ring contraction of pyrrolo[3,2,1-kl]phenothiazine. Proton NMR and mass spectral studies

Tomas Klingstedt; Anders Hallberg; Philip Dunbar; Arnold R. Martin


Journal of Heterocyclic Chemistry | 1984

Mass spectral fragmentation patterns of heterocycles. VII . Reinvestigation of fundamental processes in phenothiazines

Anders Hallberg; Ibrahim Al-Showaier; Arnold R. Martin


Journal of Heterocyclic Chemistry | 1983

Metallations of 5 H-dibenz [b, f] azepine and 10,11-dihydro-5H-dibenz [b, f] azepine. Synthesis of 4-substituted derivatives

Torsten Dahlgren; Anders Hallberg; R. Helitzer; Arnold R. Martin

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