new 3h-indole synthesis by fischer’s method. part i.新的3 h-indole费舍尔的合成方法。.pdfVIP

Molecules 2010, 15, 2491-2498; doi:10.3390/molecule OPEN ACCESS Molecules ISSN 1420-3049 /journal/molecules Article New 3H-Indole Synthesis by Fischer’s Method. Part I. Sami Sajjadifar 1,2,*, Hooshang Vahedi 1, Abdolhossien Massoudi 1 and Omid Louie 1 1 Department of Chemistry, Payame Noor University (PNU), P O Box 91735-433, Mashhad, Iran; E-Mails: hooshangvahedi@yahoo.co.uk (H.V.); Massoudi_h@pnu.ac.ir (A.M.); o_louie2001@ (O.L.) 2 Department of Chemistry, Payame Noor University (PNU), Ilam, Iran * Author to whom correspondence should be addressed; E-Mail: ss_sajjadifar@; Tel.: +98 8412228316. 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