37647-91-9Relevant academic research and scientific papers
Rearrangements of Pyrimido- and Diazepino-indoles: Syntheses of 1,5-Benzodiazocines and 1,6-Benzodiazonines
Cliffe, Ian A.,Heatherington, Kenneth,White, Alan C.
, p. 1975 - 1979 (2007/10/02)
Rearrangements of the pyrimidoindoles 1 and 2 and the pyrimidoindolinium iodide 13 produce the 1,2,3,4,5,6-hexahydro-1,5-benzodiazocines 7-9.The diazepinoindole 16 produces the 2,3,4,5,6,7-hexahydro-1,6-benzodiazonine 18.Formation of compounds 7 and 8 is less facile than that of compounds 9 and 18.The pyrimidoindoles 1 and 2 and the diazepinoindole 16 undergo rearrangement with arenesulphonyl chlorides such as toluene-p-sulphonyl chloride but not with carboxylic acid chlorides to give the diazocines 10 and 12 and the diazonine 20.Mechanisms for the rearrangements are discussed in terms of indole 2,3-oxide intermediates.The reduction of the pyrimidoindole 2 with lithium tetrahydroaluminate generates the bicyclic aminal 26.The treatment of the bicyclic lactam 11 with lithium tetrahydroaluminate or with sodium methoxide results in ring-opening and formation of the 1,2,3,4-tetrahydro- and 1,2,3,4,5,6-hexahydro-1,5-benzodiazocines 27 and 28.
