Preparation of 5‐methyl‐2‐sulfanyl‐7h‐1,3,4‐thiadiazolo[3,2‐a]‐pyrimidin‐7‐ones

7H‐1,3,4‐Thiadiazolo[3,2‐a]pyrimidin‐7‐ones can be prepared by the acylation of 5‐amino‐1,3,4‐thiadiazoles with diketene and subsequent ring closure (dehydration). Whereas arylthio substituents (SC₆H₅) can be introduced in 2‐position by the replacement of Br, alkylthio groups (SC₂H₅) have to be already presentin the starting 5‐amino‐1,3,4‐thiadiazole. The ambident nucleophile 2‐thiazolidinethione reacts in the Br substitution reaction on the N atom.     

Synthesis of new spiro‐[isothiochromene‐3,5′‐isoxazolidin]‐4(1H)‐ones

A series of seven new 2′,3′,4′‐substituted spiro[isothiochromene‐3,5′‐isoxazolidin]‐4(1H)‐ones ( 7‐13 ) has been prepared in the reaction of benzylidene(phenyl)azane oxide ( 5 ) or benzylidene(methyl)azane oxide ( 6 ) with (3Z)‐3‐(4‐substituted‐benzylidene)‐1H‐isothio‐ chromen‐4(3H)‐one ( 1‐4 ). The reaction occurs by a 1,3‐dipolar cycloaddition mechanism that leads to the regiospecific formation of various spiroisoxazolidines ( 7‐13 ).     

Synthesis of substituted amino‐cycloalkyl[b]thieno‐[3,2‐e]pyridines

An efficient two respectively three steps procedure for the synthesis of cycloalkyl[b]thieno[3,2‐e]‐pyridine amines was developed and in general good to very good yields were obtained.     

An efficient synthesis of pyrazolo[3,4‐b]pyrrolo[2,3‐d]pyridines from 5‐aminopyrazoles and cyclic β‐keto ester

5‐Chloroethylpyrazolo[3,4‐b]pyridines were synthesized by condensation of 5‐aminopyrazoles with α‐acetyl γ‐butyrolactone followed by cyclization treating with phosphorous oxychloride. 5‐Chloroethyl‐pyrazolo[3,4‐b]pyridines, thus obtained, were then converted to the corresponded tricyclic pyrazolo[3,4‐b]‐pyrrolo[2,3‐d]pyridines by treating with some primary amines.     

Ring closure reactions of 5‐azidopyrido[2,3‐d]pyrimidinetriones to isoxazolo‐ and oxadiazolopyrido[2,3‐d]pyrimidinetriones

Thermal decomposition of 5‐azidopyrido[2,3‐d]pyrimidines 2 and 7 having reactive ortho‐substituents such as a formyl or a nitro group yielded isoxazolo[3′,4′:4,5]pyrido[2,3‐d]pyrimidines 3 or oxadiazolo‐[3′,4′:4,5]pyrido[2,3‐d]pyrimidines 9. The reaction conditions of the azide decomposition were studied by differential scanning calorimetry (DSC). In addition, desoxygenation of N‐oxides 9 to oxadiazoles 10 and regioselective reduction of azides 7 to amines 8 were studied.