72922-96-4Relevant academic research and scientific papers
Synthesis of 1,2,4-Benzothiadiazines via Readily Generated Iminium Ions
Alo, Babajide I.,Adegoke, Emmanuel A.,Ligali-Ali, Mamoudou,Adesogan, E. Kayode
, p. 805 - 808 (2007/10/02)
A general method for the regiospecific synthesis of 1,2,4-benzothiadiazines, which are powerful diuretics and antihypertensive agents, has been developed.The N-arylsulphonylprolyl chlorides (5)-(7) reacted instantaneously with silver trifluoromethanesulphonate at room temperature to give the iminium salts (9)-(11) which provided the nitroamines (13)-(15) in quantitative yield.Reductive cyclisation of the nitroamines led to the tetrahydro-1H-pyrrolobenzothiadiazine 5,5-dioxide (17)-(20) in very good yields.No optimisation of yields was attempted. Efficient methods for the synthesis of some new substituted N-(nitrobenzenesulphonyl)-pyrrolidinecarboxulic acids (1)-(4), which were not readily available, are also described.
