4-azaphenothiazine

Structural formula
General
Surname	4-azaphenothiazine
other names	1 H -pyrido [3,2- b ] [1,4] benzothiazine ( IUPAC ); 10 H -Benzo [ b ] pyrido [2,3- e ] [1,4] thiazine;
Molecular formula	C 11 H 8 N 2 S
External identifiers / databases
EC number	205-973-7
ECHA InfoCard	100.005.431
PubChem	67496
Wikidata	Q229907
properties
Molar mass	200.26 g mol −1
Physical state	firmly
Melting point	114-115 ° C
safety instructions
GHS labeling of hazardous substances
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

In chemistry, 4-azaphenothiazine belongs to the group of heterocycles and is an intermediate product in the synthesis of a large number of medicinal products .

history

The first synthesis succeeded in 1958 by a Smiles rearrangement with subsequent cyclization .

Extraction and presentation

Melting N - (pyrid-2-yl) aniline with sulfur in the presence of catalytic amounts of iodine gives 4-azaphenothiazine. Alternatively, 4-azaphenothiazine can also be prepared starting from 2-chloropyridine and 2-aminothiophenol .

properties

4-Azaphenothiazine can be alkylated on the secondary amino group (NH) by reaction with haloalkanes in a basic medium. The reaction of 4-azaphenothiazine with phosgene gives 4-azaphenothiazine-10-carboxylic acid chloride, which reacts with alcohols to form urethanes , with thiols to form thiocarbamic acid esters and amines to form urea derivatives .

use

4-Azaphenothiazine is used as a starting material for the drugs prothipendyl (Dominal ^® ), isothipendyl (Andantol ^® ) and pipacetate (Selvigon ^® / Theratuss).

Individual evidence

↑ ^a ^b W. Schuler , H. Klebe: 4-Azaphenothiazines and their 10-aminoalkyl derivatives , in Liebigs Ann. 1962 , 653 , 172-180; doi: 10.1002 / jlac.19626530120 .
↑ ^a ^b data sheet 10H-PYRIDO (3,2-B) (1,4) BENZOTHIAZINE from Sigma-Aldrich , accessed on May 12, 2011 ( PDF ).
↑ HL Yale, F. Sowinski: 10- (Dialkylaminoalkyl) -pyrido [3,2-b] [1,4] benzothiazine (1-Azaphenothiazine) and Related Compounds , in: J. Am. Chem. Soc. 1958 , 80 , 1651-1654; doi: 10.1021 / ja01540a035 .
^ B. Kutscher, HR Dieter, H.-G. Trömer, B. Bartz, J. Engel, A. Kleemann : New synthesis of 4-azaphenothiazine , in: Liebigs Ann. 1995 : 591-592; doi: 10.1002 / jlac.199519950381 .
↑ W. Schuler , H. Klebe, A. von Schlichtegroll: Derivatives of 4-azaphenothiazine-10-carboxylic acid , in: Liebigs Ann. 1964 , 673 , 102-112; doi: 10.1002 / jlac.19646730114 .
^ A. von Schlichtegroll, in: Arzneimittel-Forschung 1957 , 7 , 237.
^ Wilhelm A. Schuler, Hans Klebe, Ansgar V. Schlichtegroll: Syntheses of 4-aza-phenothiazines, II. Derivatives of 4-aza-phenothiazine-10-carboxylic acid . In: Justus Liebig's Annals of Chemistry . tape 673 , no. 1 , May 4, 1964, pp. 102-112 , doi : 10.1002 / jlac.19646730114 ( PDF ).

[SCHULER-1] W. Schuler , H. Klebe: 4-Azaphenothiazines and their 10-aminoalkyl derivatives , in Liebigs Ann. 1962 , 653 , 172-180; doi: 10.1002 / jlac.19626530120 .

[Sigma-2] ta sheet 10H-PYRIDO (3,2-B) (1,4) BENZOTHIAZINE from Sigma-Aldrich , accessed on May 12, 2011 ( PDF ).

[3] HL Yale, F. Sowinski: 10- (Dialkylaminoalkyl) -pyrido [3,2-b] [1,4] benzothiazine (1-Azaphenothiazine) and Related Compounds , in: J. Am. Chem. Soc. 1958 , 80 , 1651-1654; doi: 10.1021 / ja01540a035 .

[4] B. Kutscher, HR Dieter, H.-G. Trömer, B. Bartz, J. Engel, A. Kleemann : New synthesis of 4-azaphenothiazine , in: Liebigs Ann. 1995 : 591-592; doi: 10.1002 / jlac.199519950381 .

[5] W. Schuler , H. Klebe, A. von Schlichtegroll: Derivatives of 4-azaphenothiazine-10-carboxylic acid , in: Liebigs Ann. 1964 , 673 , 102-112; doi: 10.1002 / jlac.19646730114 .

[6] A. von Schlichtegroll, in: Arzneimittel-Forschung 1957 , 7 , 237.

[7] Wilhelm A. Schuler, Hans Klebe, Ansgar V. Schlichtegroll: Syntheses of 4-aza-phenothiazines, II. Derivatives of 4-aza-phenothiazine-10-carboxylic acid . In: Justus Liebig's Annals of Chemistry . tape 673 , no. 1 , May 4, 1964, pp. 102-112 , doi : 10.1002 / jlac.19646730114 ( PDF ).