Chemistry of the Benzylpyridines. II. Nuclear Substituted 2-Benzylpyridines<sup>1</sup>

Sperber, Nathan; Papa, Domenick; Schwenk, Erwin; Sherlock, Margaret H.

doi:10.1021/ja01152a088

Cited by 31 publications

(9 citation statements)

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“…3 The isolated a-hydroxybenzyl heterocycles 1-4 were converted by reaction with thionyl chloride to their chloromethylene derivatives. The reduction of the crude product was carried out by heating with zinc powder in acetic acid 7 to afford 2-(2¢-ethylthiobenzyl)benzoxazole (5), 2-(2¢,4¢-diphenylthiobenzyl)benzoxazole (6), and their benzothiazoles analogs 7 and 8 in good yield.…”

Section: Methodsmentioning

confidence: 99%

Sulfinyl- and Sulfonyl-Substituted2-Benzylbenzoxazoles and 2-Benzylbenzothiazoles as PotentialPhotochromic Compounds

Heynderickx¹,

Guglielmetti²,

Dubest³

et al. 2003

Synthesis

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S u b s t i t u t e d 2 -B e n z y l b e n z o x a z o l e s a n d 2 -B e n z y l b e n z o t h i a z o l e s a s P o t e n t i a l P h o t o c h r o m i c C o m p o u n d sAbstract: Some novel 2-benzylbenzoxazoles and 2-benzylbenzothiazoles, substituted at the 2¢ position by electron-withdrawing groups, were synthesized via the lithiation of the benzoxazole or benzothiazole ring. The expected reversible photoinduced protontransfer reaction of such compounds was studied.

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Section: Methodsmentioning

confidence: 99%

Sulfinyl- and Sulfonyl-Substituted2-Benzylbenzoxazoles and 2-Benzylbenzothiazoles as PotentialPhotochromic Compounds

Heynderickx¹,

Guglielmetti²,

Dubest³

et al. 2003

Synthesis

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“…In the next step, treatment of alcohols 5-8 with thionyl chloride provided chloromethylene derivatives as determined by their 1 H-NMR spectrum. Then, reduction of these intermediates with Zn powder in acetic acid afforded 2-benzylpyridines 9-12 [6] (Scheme I, Table I).…”

Section: Synthesismentioning

confidence: 99%

“…for C 24 H 19 NOS 2 : C,71.79;H,4.77;N,3.49. Found: C,71.70;H,4.77;N,3.45. General Procedure for Reduction of Alcohols to Substituted 2-(Benzyl)pyridines 9-12 [6].…”

Section: -[α-Hydroxy-2-(phenylthio)benzyl]pyridine (5)mentioning

confidence: 99%

ChemInform Abstract: Synthesis of New Benzylpyridines as Potential Photochromic Compounds.

2001

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Photoinduced proton transfer systems such as 2-(2',4'-dinitrobenzyl)pyridine derivatives have been developed in an attempt to apply the compounds to variable optical transmission materials. However their fatigue resistance property is a limitation for these applications. New benzylpyridines have been synthesized and tested. 2-(2',4'-Diphenylsulfonybenzyl)pyridine was found to be photochromic in the crystalline state and in ethanolic solution (λ max = 485 nm) upon UV flash photolysis.

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“…81), and heterocyclic halides (822). Thus, the reaction of acetonitrile with 2-bromopyridine (822) gives di(2-pyridyl)acetonitrile (25 per cent).…”

Section: Amides a Alkylationmentioning

confidence: 99%

“…The methyl urethan of ethyl alcohol has been condensed with the half-amide half-ester of methyl(l-cyclohexenyl)malonic acid in the presence of sodium amide to give the corresponding barbituric acid (841). 81), and heterocyclic halides (822). Thus, the reaction of acetonitrile with 2-bromopyridine (822) gives di(2-pyridyl)acetonitrile (25 per cent).…”

Section: Amides a Alkylationmentioning

confidence: 99%

The Chemistry of the Alkali Amides.

Levine¹,

Fernelius²

1954

Chem. Rev.

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This review of the chemistry of the alkali amides is a continuation of two earlier reviews (17) which have appeared on this subject. In the present review the authors have summarized the work on the inorganic and organic chemistry of the alkali amides which has appeared in the literature from 1937 through 1952. In addition, a considerable amount of previously unpublished material is discussed. Whenever possible, the authors have tried to interpret and evaluate critically the material presented and to call attention to those areas of research which have not been investigated or which should be studied further. Although it has not been convenient to discuss all of the present material under the same headings as were used previously, the changes have not been so extensive as to make cross references difficult.

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Chemistry of the Benzylpyridines. II. Nuclear Substituted 2-Benzylpyridines¹

Cited by 31 publications

References 1 publication

Sulfinyl- and Sulfonyl-Substituted2-Benzylbenzoxazoles and 2-Benzylbenzothiazoles as PotentialPhotochromic Compounds

Sulfinyl- and Sulfonyl-Substituted2-Benzylbenzoxazoles and 2-Benzylbenzothiazoles as PotentialPhotochromic Compounds

ChemInform Abstract: Synthesis of New Benzylpyridines as Potential Photochromic Compounds.

The Chemistry of the Alkali Amides.

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Chemistry of the Benzylpyridines. II. Nuclear Substituted 2-Benzylpyridines1

Cited by 31 publications

References 1 publication

Sulfinyl- and Sulfonyl-Substituted2-Benzylbenzoxazoles and 2-Benzylbenzo­thiazoles as PotentialPhotochromic Compounds

Sulfinyl- and Sulfonyl-Substituted2-Benzylbenzoxazoles and 2-Benzylbenzo­thiazoles as PotentialPhotochromic Compounds

ChemInform Abstract: Synthesis of New Benzylpyridines as Potential Photochromic Compounds.

The Chemistry of the Alkali Amides.

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Product

Resources

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Chemistry of the Benzylpyridines. II. Nuclear Substituted 2-Benzylpyridines¹

Sulfinyl- and Sulfonyl-Substituted2-Benzylbenzoxazoles and 2-Benzylbenzothiazoles as PotentialPhotochromic Compounds

Sulfinyl- and Sulfonyl-Substituted2-Benzylbenzoxazoles and 2-Benzylbenzothiazoles as PotentialPhotochromic Compounds