Michell, Glynn; Rees, Charles W. published an article in 1987, the title of the article was Photolysis of 1-aryl-1,2,3-triazoles; rearrangement via 1H-azirines.Name: Methyl 2-methyl-1H-indole-3-carboxylate And the article contains the following content:
Naphthyltriazoles I (R = H, Me; R1, R2 = H, Me, MeC:CH2, CO2Me, CO2Et, CHO, cyano; R1 = R2 = COPh, CO2Me, CONH2, cyano) 1 were prepared from 1-azidonaphthalenes by 1,3-dipolar cycloaddition reactions. Photolysis of I (R = H, R1 = R2 = COPh, CO2Me, CONH2, cyano; R1 = CO2Et, CO2Me, cyano; R2 = H, Me) gave good yields of the expected benz[g]indoles II. I (R = H, R1 = H, Me, R2 = CO2Et, CO2Me, cyano) also gave mixtures of the expected II and rearranged II. Photolysis of 1-phenyltriazoles III (R = H, Me; R1 = CO2Me; R = CO2Me, R1 = H, Me) gave similar results; III (R = CO2Me R1 = H, Me) gave mixtures of expected and rearranged indoles IV (R = CO2Me, R1 = H, Me; R = H, Me; R1 = CO2Me) whereas III (R = H, Me; R1 = CO2Me) gave indoles IV (R = H, Me, R1 = CO2Me) only. These results are explained by a mechanism in which the less stable carbene intermediate rearranges to the more stable carbene intermediate via a 1H-azirine intermediate, in competition with its direct cyclization. Photolysis of I (R = Me, R1 = R2 = CO2Me, cyano) follows a different salts, giving high yields of deeply colored benzoquinoline derivatives V (R1 = CO2Me, cyano). The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Name: Methyl 2-methyl-1H-indole-3-carboxylate
The Article related to naphthyltriazole preparation photolysis, benzindole, indole, benzoquinoline, triazole aryl photolysis, azirine intermediate aryltriazole photochem rearrangement, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Name: Methyl 2-methyl-1H-indole-3-carboxylate
Referemce:
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