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Molecules 2010, 15(4), 2491-2498; doi:10.3390/molecules15042491
Article

New 3H-Indole Synthesis by Fischer’s Method. Part I.

1,2,* , 1
, 1
 and 1
1 Department of Chemistry, Payame Noor University (PNU), P O Box 91735-433, Mashhad, Iran 2 Department of Chemistry, Payame Noor University (PNU), Ilam, Iran
* Author to whom correspondence should be addressed.
Received: 6 February 2010 / Revised: 12 March 2010 / Accepted: 19 March 2010 / Published: 8 April 2010
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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 3H-indole; indolenine; Fischer’s synthesis method; acetic acid
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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