36893-29-5Relevant academic research and scientific papers
NEW HETEROCYCLIC SYNTHESES FROM α-HALOHYDRAZONES. REARRANGEMENTS OF α-ARYLAMINO- AND α-ARYLTHIOACYLHYDRAZONES IN ACID MEDIUM
Benincori, Tiziana,Fusco, Raffaello,Sannicolo, Franco
, p. 635 - 639 (2007/10/02)
α-(Arylamino)-acylhydrazones 1d-f react with polyphosphoric acid to give 2-arylazoindoles 3a-d through a cyclodehydration process involving the arylamino moiety.A deviation from the expected course is observed with the aldehydic substrates 1a-c which give the isatine derivatives 2a-c. α-(Arylthio)-acylhydrazones 1g-i give the 3-(arylthio)cinnolines 4b-d and 4-aminophenyl phenylsulphide 5, the latter being formed through an unprecedented rearrangement.A similar rearrangement is shown by α-phenylthio-α-phenylhydrazonobenzaldehyde, 6, which give 2-aminophenyl phenyl sulphide, 7.
