New 3H-indole synthesis by Fischer's method. Part I.
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).
Sajjadifar
Sami
S
Department of Chemistry, Payame Noor University (PNU), Mashhad, Iran. ss_sajjadifar@yahoo.com
Vahedi
Hooshang
H
Massoudi
Abdolhossien
A
Louie
Omid
O
D019342:Acetic Acid / Q000737:chemistry; D003512:Cyclohexanones / Q000737:chemistry; D006834:Hydrazines / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis*; D010422:Pentanones / Q000737:chemistry
D003512:Cyclohexanones; D006834:Hydrazines; D007211:Indoles; D010422:Pentanones; C532535:2-methylcyclohexanone; D019342:Acetic Acid; C035850:isopropyl methyl ketone