Heterocyclic Syntheses Involving Nitrilium Salts and Nitriles under Acidic Conditions

Johnson, Francis; Madronero, R.

doi:10.1016/s0065-2725(08)60576-0

Cited by 45 publications

(11 citation statements)

References 75 publications

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“…We attribute this to a stronger electron withdrawal by the dicyanomethylene group allowing a greater contribution of resonance forms like A, and even B, to the overall electronic structure (Scheme 4). In agreement with this, the high field 13 C resonance at 81.8 ppm of the central carbon of the dicyanomethylene group, compared with the analogous resonance at 108.2 ppm for TCNE, 11 indicates that substantial negative charge is located on the dicyanomethylene group of 2.…”

Section: Reaction Of Tcne With Monosulfur Dichloridesupporting

confidence: 55%

Reaction of tetracyanoethylene with SCl2; new molecular rearrangements

Koutentis

Rees

2000

J. Chem. Soc., Perkin Trans. 1

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Section: Reaction Of Tcne With Monosulfur Dichloridesupporting

confidence: 55%

Reaction of tetracyanoethylene with SCl2; new molecular rearrangements

Koutentis

Rees

2000

J. Chem. Soc., Perkin Trans. 1

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“…When this reaction was applied to o-cyanoacyl halides (6), however, a novel synthesis of wide application was found for five-membered, six-membered, and seven-membered heterocycles. Significantly, the synthesis leads directly to a heterocycle having a reactive haIogen atom.…”

Section: Electrophilic Reactions On Nitrile-hydrogen Halide Adductsmentioning

confidence: 99%

Syntheses of Heterocycles by Intramolecular Acylation of Nitrile‐Hydrogen Halide Adducts

Simchen

Entenmann

1973

Angew. Chem. Int. Ed. Engl.

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63] a) In the fast acid hydrolyses of cyclic phosphates (Section 5.3). phosphonates (Section 5.4) and in a slightly different manner, diethyl-2-carboxyphenyl phosphonate [63 b, c] ria cyclic oxyphosphoranederivatives, an equatorial hydroxyl is formed from the phosphoryl oxygen due to the constraints involved; b) M . Gordon, V A. Nataro, and C . E. Grij'n, J. Amer Chem. Soc. 86, 1898 (1964); c) G . M Blackburn and M . J. Brown, ibid. 91, 525 (1969).[72] Review articleFive-membered, six-membered, and seven-membered aza-, diaza-, and thiazaheterocycles can be prepared by cyclization of w-cyano carboxylic acid halides in the presence of hydrogen halides in aprotic solvents. Nitrite-hydrogen halide adducts occur as intermediates in this novel heterocycle synthesis of wide application. The acylating cyclizations of nitriles in protonic media, which proceed via imidic esters or amides, are not discussed.

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“…8 However, further applications have been limited so far due to the lack of suitable preparative methods and the relative instability of the anomeric 2-oxazoline ring. The Ritter reaction, 9 i.e., the generation of a relatively stable carbocation and its in situ trapping by nitriles, to give transient nitrilium species that can undergo further inter or intramolecular nucleophilic attack by a suitably located group, is an attractive strategy for the preparation of a variety of amide products and azaheterocycles that has already found utility in carbohydrate chemistry. 10 Transient glycosyl isooxazoline intermediates have been already invoked in some Ritter-like transformations.…”

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confidence: 99%