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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.

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.


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Mentions: Phenazine derivatives are an important class of condensed heterocycles of natural origin [1–4]. Selected methods of synthesizing the phenazine framework are presented in Scheme 1. One of the oldest methods is the reaction of anilines with nitroarenes under basic conditions (the Wohl–Aue reaction, path a) [5]. The Holliman synthesis of phenazines (path b) is a base-induced cyclization of ortho-nitrodiphenylamines [6]. In the Bamberger–Ham reaction (path c) nitrosobenzenes dimerize under acidic conditions to form phenazines [7]. Other methods are the condensation of ortho-phenylenediamines with ortho-quinones (path d) [8], reaction of benzofuroxanes and phenols (the Beirut reaction, path e) [9], and palladium-catalyzed cyclization of 2-amino-2′-bromophenylenediamines (path f) [10].


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: Phenazine derivatives are an important class of condensed heterocycles of natural origin [1–4]. Selected methods of synthesizing the phenazine framework are presented in Scheme 1. One of the oldest methods is the reaction of anilines with nitroarenes under basic conditions (the Wohl–Aue reaction, path a) [5]. The Holliman synthesis of phenazines (path b) is a base-induced cyclization of ortho-nitrodiphenylamines [6]. In the Bamberger–Ham reaction (path c) nitrosobenzenes dimerize under acidic conditions to form phenazines [7]. Other methods are the condensation of ortho-phenylenediamines with ortho-quinones (path d) [8], reaction of benzofuroxanes and phenols (the Beirut reaction, path e) [9], and palladium-catalyzed cyclization of 2-amino-2′-bromophenylenediamines (path f) [10].

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.