Advances in the Chemistry of Pernitriles

Зефиров, Н. С.; Makhon'kov, D. I.

doi:10.1070/rc1980v049n04abeh002463

Cited by 17 publications

(4 citation statements)

References 6 publications

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“…There are some other types of "X-ation" reactions, but they have not yet received appreciable application. agent,54-56,132 134 as illustrated in eq 32. The cyanophilic…”

Section: Synthetic Applications Of X-phlllc Reactionsmentioning

confidence: 99%

X-philic reactions

Зефиров¹,

Makhon'kov²

1982

Chem. Rev.

201

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“…There are some other types of "X-ation" reactions, but they have not yet received appreciable application. agent,54-56,132 134 as illustrated in eq 32. The cyanophilic…”

Section: Synthetic Applications Of X-phlllc Reactionsmentioning

confidence: 99%

X-philic reactions

Зефиров¹,

Makhon'kov²

1982

Chem. Rev.

201

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“…Also, it can act as an umpolung source of dicyanomethylene . The addition of nucleophiles to the double bond of TCNE, subsequently loss cyanide afforded tricyanovinylation intermediates , which is the common reaction. On the other hand, direct addition to one of the nitrile groups can also occur but is less frequent .…”

Section: Introductionmentioning

confidence: 99%

Novel Synthesis of 1,3‐Thiazine and Pyrimidinethione Derivatives from (1‐Aryl ethylidene)hydrazinecarbothioamides and Tetracyanoethylene

Hassan

Ibrahim

El‐Sheref

et al. 2015

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).1,3-Thiazine-5,6,6-tricarbonitrile and 2-thioxo-2,3-dihydropyrimidine-4,5-dicarbonitriles derivatives were synthesized via interactions between (1-aryl ethylidene)hydrazinecarbothioamides and tetracyanoethylene to give the derivatives of tetracyanoethane and tricyanovinylation intermediates, followed by heterocyclization. The structures of the products have been confirmed by different spectroscopic analyses. A rational for the formation of the products is presented.

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“…11,12 The chemistry of TCNE has been extensively reviewed. 7,13−19 With primary or secondary aliphatic amines and with most primary and secondary aromatic amines, the reaction with TCNE gives N-tricyanovinylamines 1, although with an excess of amine, 1,1-diamino-2,2-dicyanoethylenes 2 13,20,21 or 1,2diamino-1,2-dicyanoethylenes 3 22 are formed. TCNE does not react with tertiary aliphatic amines, but it readily reacts with both tertiary and secondary aromatic amines, attacking the arene to give 4-tricyanovinyl-arylamines 4 via the initial formation of a 1:1 π complex.…”

Section: Introductionmentioning

confidence: 99%

Reactions of Tetracyanoethylene withN′-Arylbenzamidines: A Route to 2-Phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles

2013

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Eight 2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles 15 are prepared in four steps from N'-arylbenzamidines 11 and tetracyanoethylene (TCNE) in ~70-90% yields. The transformation involves the initial formation of N-aryl-N'-(1,2,2-tricyanovinyl)benzamidines 12 in 87-99% yields, which in MeCN undergo a 5-exodig cyclization to give the 2-[1-aryl-5-imino-2-phenyl-1H-imidazol-4(5H)-ylidene]malononitriles 13 in 84-92% yields, while in MeOH the (Z)-2-[2-phenyl-4-(arylimino)-1H-imidazol-5(4H)-ylidene]malononitriles 14 are formed in 85-94% yields. The imidazoles 14 can also be prepared directly from imidazoles 13 via a Dimroth rearrangement in either neat MeOH or in DCM with DBU. Subsequent thermolysis of imidazoles 14 in diphenyl ether affords 2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles 15 in near quantitative yields. Mechanistic rationale is provided for all transformations.

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Advances in the Chemistry of Pernitriles

Cited by 17 publications

References 6 publications

X-philic reactions

X-philic reactions

Novel Synthesis of 1,3‐Thiazine and Pyrimidinethione Derivatives from (1‐Aryl ethylidene)hydrazinecarbothioamides and Tetracyanoethylene

Reactions of Tetracyanoethylene withN′-Arylbenzamidines: A Route to 2-Phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles

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