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

被引：18

作者：

Sajjadifar, Sami ^{[1
,2
]}

Vahedi, Hooshang ^{[1
]}

Massoudi, Abdolhossien ^{[1
]}

Louie, Omid ^{[1
]}

机构：

[1] PNU, Dept Chem, Mashhad, Iran

[2] PNU, Dept Chem, Ilam, Iran

来源：

MOLECULES | 2010年 / 15卷 / 04期

关键词：

3H-indole; indolenine; Fischer's synthesis method; acetic acid; INDOLE SYNTHESIS; CYCLIZATION; DIRECTION;

D O I：

10.3390/molecules15042491

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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).

引用

页码：2491 / 2498

页数：8

共 15 条

[1] The use of N-15 as a tracer element in chemical reactions - The mechanism of the Fischer indole sinthesis [J].