Angular heterocycles. A convenient synthesis of azabenzophenothiazines

Abstract

The acid‐catalysed reaction of substituted 1,4‐naphthoquinones with o‐aminoheterocyclic thiones in alcoholic solution afforded substituted monoazabenzo[a]phenothiazin‐5‐ones 4,5 and substituted benzo[a][1,4]diazabenzothiazino[3,2‐c]phenothiazin‐5‐one (6). Some of the resulting compounds were subjected to dehalogenation. The structures of the products were assigned by elemental analysis, 1H‐nmr, and other spectral analysis.

Fuctionalization of Linear and Angular Phenothiazine and Phenoxazine Ring Systems via Pd(0)/XPhos Mediated Suzuki‐Miyaura Cross‐coupling Reactions

“…Reports disclosed that phenoxazine derivatives are widely applied as organic light‐emitting diodes . The earliest modification of the structure of the parent compounds 1 and 2 in which benzene rings are fused to the sides of ring A and/or C results in nonlinear phenothiazine and phenoxazine rings of which benzo[a]phenothiazine and benzo[a]phenoxazine 3 and their derivatives were the most popular ones .…”

Synthesis of Arylnaphthoquinones and Their Reactions with o‐Substituted Primary Aromatic Amines

“…In con tin u a tion of our study for the syn the sis of heterocyclic ni tro gen dervatives, [1][2][3][4][5][6] we were in ter ested in the re action of arylnaphthoquinones with thioglycolic acid and primary ar o matic amines giv ing two types of the con den sa tion prod ucts. 6 The quin oxa line, 4,7-14 phenazine, [15][16][17][18] phenoxazine 15,19 and phe no thi azine, 20,21 ring sys tems have been ex ten sively stud ied and many such com pounds have now be come commer cially avail able and are widely used in med i cal practice 22,23 and in the dye in dus try. 24 This led us to syn the size some new re lated com pounds.…”