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Synthesis of pyrrolo[3,2-a]phenazines from 5-nitroindoles and anilines.

Wróbel Z, Więcław M, Bujok R, Wojciechowski K - Monatsh. Chem. (2013)

Bottom Line: Anilines react with 5-nitroindoles in the presence of t-BuOK in N,N-dimethylformamide (DMF) to form 5-nitroso-4-arylaminoindoles that in turn when treated with N,O-bis(trimethylsilyl)acetamide cyclize to pyrrolo[3,2-a]phenazines.In an alternative approach pyrrolo[3,2-a]phenazines are formed from aminoindoles and nitroarenes.

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Affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, P.O. Box 58, 01-224 Warsaw, Poland.

ABSTRACT

Abstract: Anilines react with 5-nitroindoles in the presence of t-BuOK in N,N-dimethylformamide (DMF) to form 5-nitroso-4-arylaminoindoles that in turn when treated with N,O-bis(trimethylsilyl)acetamide cyclize to pyrrolo[3,2-a]phenazines. In an alternative approach pyrrolo[3,2-a]phenazines are formed from aminoindoles and nitroarenes.

No MeSH data available.


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Mentions: The classic Wohl-Aue synthesis of phenazines consists in the reaction of anilines with nitroarenes under harsh basic conditions, usually by heating of both starting materials with sodium or potassium hydroxide at 200 °C [5]. In recent years we extensively studied nucleophilic aromatic substitution reactions of hydrogen in nitroarenes [11–15]. During these studies we have found that anilines react with nitrobenzene derivatives under mild conditions in the presence of t-BuOK in DMF at −50 °C to form 2-nitrosodiphenylamines that in turn upon treatment with acetic acid cyclized to phenazines (Scheme2) [16, 17].


Synthesis of pyrrolo[3,2-a]phenazines from 5-nitroindoles and anilines.

Wróbel Z, Więcław M, Bujok R, Wojciechowski K - Monatsh. Chem. (2013)

© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4495017&req=5

Mentions: The classic Wohl-Aue synthesis of phenazines consists in the reaction of anilines with nitroarenes under harsh basic conditions, usually by heating of both starting materials with sodium or potassium hydroxide at 200 °C [5]. In recent years we extensively studied nucleophilic aromatic substitution reactions of hydrogen in nitroarenes [11–15]. During these studies we have found that anilines react with nitrobenzene derivatives under mild conditions in the presence of t-BuOK in DMF at −50 °C to form 2-nitrosodiphenylamines that in turn upon treatment with acetic acid cyclized to phenazines (Scheme2) [16, 17].

Bottom Line: Anilines react with 5-nitroindoles in the presence of t-BuOK in N,N-dimethylformamide (DMF) to form 5-nitroso-4-arylaminoindoles that in turn when treated with N,O-bis(trimethylsilyl)acetamide cyclize to pyrrolo[3,2-a]phenazines.In an alternative approach pyrrolo[3,2-a]phenazines are formed from aminoindoles and nitroarenes.

View Article: PubMed Central - PubMed

Affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, P.O. Box 58, 01-224 Warsaw, Poland.

ABSTRACT

Abstract: Anilines react with 5-nitroindoles in the presence of t-BuOK in N,N-dimethylformamide (DMF) to form 5-nitroso-4-arylaminoindoles that in turn when treated with N,O-bis(trimethylsilyl)acetamide cyclize to pyrrolo[3,2-a]phenazines. In an alternative approach pyrrolo[3,2-a]phenazines are formed from aminoindoles and nitroarenes.

No MeSH data available.