Investigation of interaction of benzoquinones and naphthoquinones with substituted hydrazides

Abstract

Nucleophilic attack by substituted hydrazides on C‐2, C‐3 of 2,3,5,6‐tetrachloro‐1,4‐benzoquinone and 2,3‐dichloro‐1,4‐naphthoquinone initiates the formation of benzo[e][1,3,4]oxadiazine and benzo‐ as well as naphthoxadiazepine derivatives. On the other hand, substituted hydrazides attack 1,4‐naphthoquinone‐2,3‐dicarbonitrile to form benzo[f]indazole‐4,9‐dione derivatives. A rationale for the conversions observed is presented. J. Heterocyclic Chem., 2010.

Elaboration of Benzoxadiazepine and Benzotriazocine Scaffolds

“…proposed a one-pot synthesis involving a carbohydrazide as key intermediate. [34] In this sequence, N,N-dimethylformamide (DMF) used as solvent, had a crucial role since it performed a relevant transformation of chloranil into amide analog that subsequently reacted with heteroarylhydrazides (Scheme 13). With the aim to access potentially bioactive molecules, this reaction sequence was extended [35] with the use of fatty acid hydrazide to introduce fatty alkyl or alkenyl chain on benzo[f] [1,3,4]oxadiazepine ring (Scheme 13).…”

Chemistry and heterocyclization of carbohydrazides

“…In a different manner, 1,4‐naphthoquinone‐2,3‐dicarbonitrile 92 reacted with 1 to give substituted benzo[ f ]indazoledione 96 [66]. …”

“…A mixture of 2,3,5,6‐tetrachloro‐1,4‐benzoquinone 213 and 1 in DMF with admission of air afforded substituted benzo[1,3,4]oxadiazinecarboxamide 218 [66]. …”

“…On the other hand, the reaction of 2,3‐dichloro‐1,4‐naphthoquinone 228 with 1 in DMF afforded substituted naphtho[2,3‐ f ]‐1,3,4‐oxadiazepine‐5,6,11‐(4 H )‐trione 230 [66]. …”