Synthesis of 1,5-Diamino-1,5-dihydrobenzobistriazole (DABT) and Its Use as a 1,4-Benzadiyne Equivalent

Article abstract of DOI:10.1021/jo00357a005

Amination of 1,5-dihydrobenzo<1,2-d:4,5-d'>bistriazole (9) gives the 1,5- and 1,7-diamino derivatives 3 and 10 both useful as 1,4-benzadiyne equivalents, as well as the 1,6 isomer 11 and the recyclable monoamino derivatives 12 and 13.Sixteen examples of the synthetic utility of DABT (3) with lead tetraacetate in bisannulations are described (Table 1).The aryne-trapping dienes include ester, halogen, and carbonyl functionality; often the reactions are quite regio- and stereoselective as a consequence of the stepwise nature of the annulations.