Chemistry is the experimental and theoretical study of materials on their properties at both the macroscopic and microscopic levels.In a patent， Application In Synthesis of Ethyl 5-chloro-6-fluoro-1H-indole-2-carboxylate, Which mentioned a new discovery about 473257-60-2
Dye-sensitized photooxygenations of cyclic and acyclic 1,4-diaza-1,3-butadienes (alpha-Diimines), carrying a methyl or an ethyl group in the 2-position, yield isonitriles and amides, as well as formaldehyde or acetaldehyde.Thus, cyclic alpha-diimines such as 5,6-dimethyl- (1a), 5-methyl-6-phenyl- (1b), 5-methyl-6-(p-tolyl)- (1c), and 5,6-diethyl-2,3-dihydropyrazine (1d) yield the respective 1-isocyano-2-(acylamino)ethanes 2a-d, whereas 5-isopropyl-6-phenyl- (1e) and 5,6-diphenyl-2,3-dihydropyrazine (1f) are inert toward photooxygenation.Acyclic alpha-diimines such as 1,8-bis(acetylamino)-3,6-diaza-4,5-dimethyl-3,5-octadiene (4a), 2,5-diaza-3,4-dimethyl-2,4-hexadiene (4b), 1,4-diaza-2,3-dimethyl-1,4-diphenyl-1,3-butadiene (4c), and N,N’-bis<(1S,2S,3S,5R)-pinan-3-ylmethyl>-2,3-butanediimine (4d) afford the respective isonitriles 5a-d and acetamides 6a-d.With retention of configuration, chiral alpha-diimines such as (-)-N,N’-bis<(S)-1-phenylethyl>-2,3-butanediimine <(S,S)-4e> and its R,R enantiomer <(R,R)-4e>, and (3S,8S)-(-)-3,8-dicarbomethoxy-4,7-diaza-2,5,6,9-tetramethyl-4,6-decadiene <(S,S)-4f> yield the corresponding enantiomerically pure isonitriles (S)-5e, (R)-5e, and (S)-5f and acetamides (S)-6e, (R)-6e, and (S)-6f.Evidence for a singlet oxygen reaction is presented.A working hypothesis is proposed which includes the formation of a transient hydroperoxide 7 that fragments into an isonitrile molecule, an aldehyde, and an N-alkyl- or N-arylnitrilium cation and a hydroxide ion; the latter combine to yield the amide groups in 2a-d and the amide compounds 6a-f.
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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