The reaction of 2-amino- N ′-arylbenzamidines with tetracyanoethene reinvestigated: routes to imidazoles, quinazolines and quinolino[2′,3′:4,5]imidazo[1,2- c ]quinazoline-8-carbonitrile

The Reaction of 2-Amino-N'-arylbenzamidines with Tetracyanoethene Reinvestigated: Routes to Imidazoles, Quinazolines and Quinolino[2',3':4,5]imidazo[1,2-c]quinazoline-8-carbonitrile. -The reaction of 2-amino-N-arylbenzamidines with tetracyanoethene is investigated under different reaction conditions to provide either imidazoline of type (III), quinazolines (IV) or (V) as sole or main products. An independent synthesis of imidazoline (IIIa) is also developed and the conversion to the polycyclic heterocycle (XII) is shown. -(MIRALLAI, S. I.; MANOLI, M.; KOUTENTIS*, P. A.; Tetrahedron 71 (2015) 46, 8766-8780, http://dx.

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ChemInform Abstract: The Reaction of 2‐Amino‐N′‐arylbenzamidines with Tetracyanoethene Reinvestigated: Routes to Imidazoles, Quinazolines and Quinolino[2′,3′:4,5]imidazo[1,2‐c]quinazoline‐8‐carbonitrile.

Mirallai

Manoli

Koutentis

2016

ChemInform

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Reactions of tetracyanoethylene with dimethyl/arylhydrazines and arylamines

Ivanova,

Nasakin,

Maryasov

et al. 2023

Mendeleev Communications

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Reactions of Tetracyanoethylene with Aliphatic and Aromatic Amines and Hydrazines and Chemical Transformations of Tetracyanoethylene Derivatives

Ivanova,

Osipova,

Kadyrov

et al. 2024

Molecules

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The significant synthetic potential and reactivity of tetracyanoethylene (TCNE) have captured the interest of numerous chemical communities. One of the most promising, readily achievable, yet least explored pathways for the reactivity of TCNE involves its interaction with arylamines. Typically, the reaction proceeds via tricyanovinylation (TCV); however, deviations from the standard chemical process have been observed in some instances. These include the formation of heterocyclic structures through tricyanovinyl intermediates, aliphatic dicarbonitriles through the cleavage of the C–C bond of a tetracyanoethyl substituent, complexation, and various pericyclic reactions. Therefore, the objective of this study is to review the diverse modes of interaction of TCNE with aromatic nitrogen-containing compounds and to focus the attention of the chemical community on the synthetic capabilities of this reagent, as well as the various biological and optical activities of the structures synthesized based on TCNE.

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The reaction of 2-amino- N ′-arylbenzamidines with tetracyanoethene reinvestigated: routes to imidazoles, quinazolines and quinolino[2′,3′:4,5]imidazo[1,2- c ]quinazoline-8-carbonitrile

Cited by 3 publications

References 40 publications

ChemInform Abstract: The Reaction of 2‐Amino‐N′‐arylbenzamidines with Tetracyanoethene Reinvestigated: Routes to Imidazoles, Quinazolines and Quinolino[2′,3′:4,5]imidazo[1,2‐c]quinazoline‐8‐carbonitrile.

ChemInform Abstract: The Reaction of 2‐Amino‐N′‐arylbenzamidines with Tetracyanoethene Reinvestigated: Routes to Imidazoles, Quinazolines and Quinolino[2′,3′:4,5]imidazo[1,2‐c]quinazoline‐8‐carbonitrile.

Reactions of tetracyanoethylene with dimethyl/arylhydrazines and arylamines

Reactions of Tetracyanoethylene with Aliphatic and Aromatic Amines and Hydrazines and Chemical Transformations of Tetracyanoethylene Derivatives

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