Regioselective Synthesis of 2‐oxo‐2,8‐dihydro‐[l,2,4] oxadiazolo [2,3‐<i>a</i>]pyrimidine‐7‐carbamates: A New Class of Antihypertensive Peripheral Vasodilators

The 2-oxo-2H-[ 1,2,4]oxadiazolo [2,3-a]pyrimidine-7-carbamate 3 belongs to a new class of potent peripheral vasodilators. This compound was shown to exert a strong and long-lasting antihypertensive effect in experimental animals as well as in humans [l]. Its synthesis was previously reported [2], the last step being a highly regioselective cyclization of the pyrimidine-N-oxide dicarbamate 2 (Scheme 1). Subsequently, we examined this reaction in more detail and found that thermal ring closure of 2 led to a 95 : 5 mixture of the regioisomers 3 and 4. The structure of the major isomer 3 has been unequivocally established before by an X-ray crystallographic analysis [2 b]. The minor component, isolated from the mother liquor by high pressure liquid chromatography, was identified as 4 on the basis of its spectroscopic properties.

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Regioselective Synthesis of 2‐oxo‐2,8‐dihydro‐[l,2,4] oxadiazolo [2,3‐a]pyrimidine‐7‐carbamates: A New Class of Antihypertensive Peripheral Vasodilators

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ChemInform Abstract: REGIOSELECTIVE SYNTHESIS OF 2‐OXO‐2,8‐DIHYDRO‐(1,2,4)OXADIAZOLO(2,3‐A)PYRIMIDINE‐7‐CARBAMATES: A NEW CLASS OF ANTIHYPERTENSIVE PERIPHERAL VASODILATORS

Synthesis of 2‐Oxo‐2H‐[1,2,4]oxadiazolo‐[2,3‐c]pyrimidine‐5‐carbamates

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