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N-Formylindoles (1A-H) exhibit pronounced aldehydic character as revealed by the formation of 4-nitrophenylhydrazones (2A-E) and 2,4-dinitrophenylhydrazones (2F-J).The N-formylindoles (1E-G) bearing phenyl groups at 2- and 3-positions do not form either 4-nitrophenylhydrazones or 2,4-dinitrophenylhydrazones probably owing to steric hindrance.The N-formylindoles (1C-F) which bear a substituent at 2-position but none at 7-position exist only in one conformation, while those bearing either substituents at both 2- and 7-positions (i. e. 1G) or no substituent at all (i. e. 1A, 1B) exist in two conformations as shown by their PMR spectra.While the 4-nitrophenylhydrazones (2A-E) show expected fragmentation pattern, the 2,4-dinitrophenylhydrazones exhibit some interesting fragmentation pathways involving the successive loss of two OH radicals and N2 under electron impact.

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Reference:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles