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Paper | Regular issue | Vol 43, No. 8, 1996, pp. 1665 - 1679
Published online:
DOI: 10.3987/COM-96-7488
Formation of Spiro-Lactols upon Reaction of Ninhydrin with Methyldiazines

Gottfried Heinisch, Wolfgang Holzer,* Kurt Mereiter, Barbara Strobl, and Changtu Zheng

*Institute of Pharmaceutical Chemistry, University of Vienna, Althanstrasse14, A-1090 Vienna, Austria

Abstract

Reaction of ninhydrin (4) with 4-methylpyridazine or 4-methylquinoline leads to 2-hydroxy-2-heteroarylmethyl-1,3-indandiones (5), which resist dehydration to the corresponding 2-heteroarylmethylene-1,3-indandiones (2). In contrast, employing methyl(di)azines with a methyl group in α-position to a ring nitrogen atom (3-methylpyridazine, 4-methylpyrimidine, 2-methylpyrazine, 2-methylquinoline, 2-methylquinoxaline) results in the exclusive formation of novel 3a’,8b’-dihydroxy-3’-heterozryl-3a’,8b’-dihydrospiro[indane-2,2’(3’H)-4’H-indeno[1,2-b]furan]-1,3,4’-triones (7) which might result from cyclisation of initially formed 2,2’-dihydroxy-2,2’-(heteroarylmethylene)bis-1,3-indandiones (6).

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