%0 Journal Article
%T New 3H-Indole Synthesis by Fischer¡¯s Method. Part I.
%A Sami Sajjadifar
%A Hooshang Vahedi
%A Abdolhossien Massoudi
%A Omid Louie
%J Molecules
%D 2010
%I MDPI AG
%R 10.3390/molecules15042491
%X Methyl indolenines (4a-c) and(5a-c) were prepared in high yield by a Fischer indole synthesis reaction of o,m-tolylhydrazine hydrochlorides (1a-b) with isopropyl methyl ketone (2) and 2-methylcyclohexanone (3) in acetic acid at room temperature. o,p- Nitrophenylhydrazines (1c-d) were reacted with 2-methylcyclohexanone (3) in acetic acid at reflux to give nitroindolenines (5d-e), while the attempted reactions of o,p-nitrohydrazines with isopropyl methyl ketone (2) in acetic acid were not successful. Compounds(1c-d) were reacted with isopropyl methyl ketone (2) in acetic acid/HCl to give 2,3,3-trimethyl-5-nitro-indolenine (4e) and 2,3,3-trimethyl-7-nitroindolenine (4d).
%K 3H-indole
%K indolenine
%K Fischer¡¯s synthesis method
%K acetic acid
%U http://www.mdpi.com/1420-3049/15/4/2491