《Studies on the N-oxides of π-deficient N-heteroaromatics. XXXIV. Studies on oxazepine derivatives. X. A novel synthesis of substituted indoles by photochemical ring contraction of 3,1-benzoxazepines》 was written by Kaneko, Chikara; Fujii, Harue; Kawai, Shinji; Yamamoto, Atsushi; Hashiba, Kazuhiko; Kimata, Toshihiko; Hayashi, Reiko; Somei, Masanori. Name: 3-Chloro-1H-indole-2-carbonitrile And the article was included in Chemical & Pharmaceutical Bulletin on April 30 ,1980. The article conveys some information:
A novel photochem. ring-contraction reaction of 3,1-benzoxazepines I (R = cyano, Ph; R1 = Cl, CO2H; R2 = H) yields 3-formylindoles II (R3 = CHO, R4 = H, Cl) in an aprotic solvent. This ring contraction was successfully extended to oxazepines having an alkoxycarbonyl function at the 5-position to give the indoles having this function at the 3-position. Though most of the oxazepines underwent the ring-contraction reaction only on irradiation at 254 nm, 5-carboxy derivatives or their esters afforded the ring-contraction products even at ≥300 nm. The intermediacy of 3H-indole species in these photochem. ring-contraction reactions was demonstrated by the isolation of II (R = Ph, R3 = Ac, R4 = 5-CO2Me) during the photolysis of I (R = Ph, R1 = COOMe, R2 = Me) this 3H-indole afforded II (R = Ph, R3 = Ac, R4 = 4-, and 6-CO2Me) upon further irradiation The mechanism of this acetyl migration is discussed based on the result of the photochem. acetyl migration of Me 1-acetyl-2-phenylindole-3-carboxylate. The oxazepines were obtained by photochem. rearrangement of quinoline oxides at ≥300 nm. The experimental process involved the reaction of 3-Chloro-1H-indole-2-carbonitrile(cas: 74960-46-6Name: 3-Chloro-1H-indole-2-carbonitrile)
3-Chloro-1H-indole-2-carbonitrile(cas: 74960-46-6) is a member of organic chlorides. Organic chlorides are compounds containing a carbon-chlorine bond, which are widely used in the oil field as a wax dissolver. They are generally not present in crude oils and are typically the result of additives, cleaning solutions or chemicals used for oil recovery.Name: 3-Chloro-1H-indole-2-carbonitrile
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts