Benzothiazine derivatives

Details Benzothiazine derivatives Benzothiazine derivatives

1981-08-24

1982-11-09

Ford, John M.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

544 14, C07D51322, C07D51522

Patent

active

043584071

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD AND DISCLOSURE OF THE INVENTION

This invention relates to novel benzothiazine derivatives represented by the formula ##STR2## wherein R.sub.1 is hydrogen, alkyl, alkoxycarbonyl, alkoxalyl, phenyl which may optionally have a substituent or substituents, cycloalkyl or aralkyl, R.sub.2 is hydrogen or alkyl, X is sulphur or oxygen, and Y is methylene or ethylene, and acid addition salts thereof, and also concerns with processes for preparing them.
Hereinafter the symbols in the formula (I) are more specifically described. The alkyl groups in the formula (I) refer to straight-chain or branched groups having 1 to 10 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, octyl, nonyl, decyl, etc. Examples of the cycloalkyl groups in the formula (I) are cyclopropyl, cyclopentyl, cyclohexyl, etc. Examples of the alkoxycarbonyl groups therein are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, etc. The alkoxalyl groups therein include methoxalyl, ethoxalyl, propoxalyl and butoxalyl. The phenyl groups which may have a substituent or substituents are those which may have 1 to 3 substituents such as halogen (e.g. chlorine or bromine), lower alkyl (e.g. methyl, ethyl, propyl or butyl) or lower alkoxy (e.g. methoxy, ethoxy, propoxy, butoxy or methylenedioxy) at optional position(s) in optional combinations. Examples of the aralkyl groups are .alpha.-methylbenzyl, phenetyl, etc.
The compounds represented by the formula (I) are prepared for example by processes as described below.


Process 1

This process comprises the step of reacting a compound having the formula ##STR3## with an iodine and a compound having the formula ##STR4## The symbols in the formulae (II) and (III) are as defined above.
This reaction is conducted in an inactive solvent (such as chloroform, dioxane and dimethylformamide) or without a solvent at room temperature or, when required, by heating.


Process 2

This process comprises the steps of reacting the compound of the formula (II) with a halogen to prepare a compound represented by the formula ##STR5## wherein Hal is bromine, chlorine or like halogens and Y is as defined above and reacting the compound of the formula (IV) with the compound of the formula (III).
This reaction is carried out in an inactive solvent (such as chloroform, ether, dioxane, ethanol or a mixture thereof) at room temperature or, if required, by heating the solvent up to its boiling point.


Process 3

This process is used to prepare compounds of the formula (I) wherein R.sub.1 is alkyl, cycloalkyl, alkoxycarbonyl, alkoxalyl, aralkyl and R.sub.2 is hydrogen, namely compounds of the formula ##STR6## wherein R.sub.3 is alkyl, cycloalkyl, alkoxycarbonyl, alkoxalyl, aralkyl, and X and Y are as defined above. The process comprises the step of reacting a compound represented by the formula ##STR7## wherein X and Y are as defined above with a compound of the formula like reactive residues, and R.sub.3 is as defined above.
This reaction is usually effected in an inactive solvent (such as methanol, ethanol, dioxane or dimethylformamide) and, if required, in the presence of a deoxidizer (such as pyridine, triethylamine or like organic bases, or sodium carbonate, potassium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide or like inorganic bases) at room temperature or by heating the solvent up to its boiling point.


Process 4

This process is used to prepare compounds of the formula (I) wherein R.sub.2 is alkyl, namely compounds of the formula ##STR8## wherein R.sub.4 is alkyl, and R.sub.1, X and Y are as defined above. The process comprises the step of reacting a compound of the formula ##STR9## wherein the symbols are as defined above with a compound of the formula
The reaction is carried out under the same conditions as in Process 3.


Process 5

This process is used to prepare compounds of the formula (I) wherein (R.sub.1)(R.sub.2)N-- is (R.sub.5)(R.sub.6)CHNH--, namely compounds of the formula ##STR10## wherein R.sub.5 is hydrogen

REFERENCES:
patent: 3555018 (1971-01-01), Davis
patent: 4219550 (1980-08-01), Rajagopalan

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