Tetrahedron

Divergent cyclisations of 2-(5-amino-4-carbamoyl-1H-pyrazol-3-yl) acetic acids with formyl and acetyl electrophiles

…, TP Matthews, PN Horton, MB Hursthouse, I Collins

Index: Smyth, Lynette A.; Matthews, Thomas P.; Horton, Peter N.; Hursthouse, Michael. B.; Collins, Ian Tetrahedron, 2007 , vol. 63, # 39 p. 9627 - 9634

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Citation Number: 8

Abstract

The reaction of 2-(5-amino-4-carbamoyl-1-methyl-1H-pyrazol-3-yl) acetic acid and triethylorthoformate did not give the expected dihydropyrazolo [4, 3-c] pyridin-4-one product as described in literature, but formed an alternative cyclic imide product, fully characterised by NMR and X-ray crystallography. This mode of reaction was shown to be general to other 1-substituted-2-(5-amino-4-carbamoyl-1H-pyrazol-3-yl) acetic acids. The outcome of the ...