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Reduction of imidazolium salts – An approach to diazocines and diazocanes

Tetrahedron 2017, 73 (49), 6942-6953

DOI: 10.1016/j.tet.2017.10.053

Shvydenko T.; Nazarenko K.; Shvydenko K.; Boron S.; Gutov O.; Tolmachev A.; Kostyuk A.
A convenient approach to diazocine derivatives 8,9 starting from 1,2-polymethyle-neimidazolium salts 4 was developed. The polymethylenimidazolium salts 4 are partially reduced with sodium borohydride in DMF to give 5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-a]imidazoles 5 or under more forcing conditions – (sodium triacetoxyborohydride in acetic acid) with cleavage of the endocyclic C–N bond affording diamines 6. Tertiary salts 7 readily prepared from compounds 5 react with NaBH4 and KCN nucleophiles with cleavage of the endocyclic N–C bond to form diazocine derivatives 8,9.

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