A convenient synthesis of benzannelated diazacycloalkanes by reductive cleavage of 1,2-polymethylenebenzimidazoles

Shvidenko, Tatyana; Nazarenko, Kostiantyn; Shvidenko, Konstantin; Kostyuk, Aleksandr

A convenient synthesis of benzannelated diazacycloalkanes by reductive cleavage of 1,2-polymethylenebenzimidazoles

2014

Shvidenko, Tatyana | Nazarenko, Kostiantyn | Shvidenko, Konstantin | Kostyuk, Aleksandr

A facile procedure for the synthesis of benzannelated diazacycloalkanes 3 is elaborated on the basis of reductive cleavage of 1,2-polymethylenebenzimidazoles 2 with DIBAL-H. The reduction of the corresponding salts prepared by treatment of 1,2-polymethylenebenzimidazoles 2 with methyl iodide proceeded differently affording exclusively o-phenylenediamines 10. The limitations and scope of the method were established, and a tentative mechanism proposed.

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