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New 3H-Indole Synthesis by Fischer’s Method. Part I.
Department of Chemistry, Payame Noor University (PNU), P O Box 91735-433, Mashhad, Iran
Department of Chemistry, Payame Noor University (PNU), Ilam, Iran
* Author to whom correspondence should be addressed.
Received: 6 February 2010; in revised form: 12 March 2010 / Accepted: 19 March 2010 / Published: 8 April 2010
Abstract: 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).
Keywords: 3H-indole; indolenine; Fischer’s synthesis method; acetic acid
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Cite This Article
MDPI and ACS Style
Sajjadifar, S.; Vahedi, H.; Massoudi, A.; Louie, O. New 3H-Indole Synthesis by Fischer’s Method. Part I.. Molecules 2010, 15, 2491-2498.
Sajjadifar S, Vahedi H, Massoudi A, Louie O. New 3H-Indole Synthesis by Fischer’s Method. Part I.. Molecules. 2010; 15(4):2491-2498.
Sajjadifar, Sami; Vahedi, Hooshang; Massoudi, Abdolhossien; Louie, Omid. 2010. "New 3H-Indole Synthesis by Fischer’s Method. Part I.." Molecules 15, no. 4: 2491-2498.