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Cited by 6 publications
(9 citation statements)
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“…While continuing our systematic investigations of the chemistry of tetrahydropyridines [7][8][9], we studied the question of how the ratio of the expected products is affected by the presence of an aryl substituent at C(4) in the anhydro base (the N-ylide A) generated from 1-ethoxycarbonylmethyl-1-methyl-4-phenyl-1,2,3,6-tetrahydropyridinium chloride (1) when it is heated in the presence of sodium hydride. We found that the presence of a phenyl substituent has a substantial effect on the direction of the reaction: we isolated two compounds from the reaction mixture in 1.5:1 ratio with overall yield 64%, where the first compound had the structure of the expected 4-phenylpyrrolidine 2 while the other compound, to our surprise, proved to be the tetrahydroazepine 3.…”
mentioning
confidence: 99%
“…While continuing our systematic investigations of the chemistry of tetrahydropyridines [7][8][9], we studied the question of how the ratio of the expected products is affected by the presence of an aryl substituent at C(4) in the anhydro base (the N-ylide A) generated from 1-ethoxycarbonylmethyl-1-methyl-4-phenyl-1,2,3,6-tetrahydropyridinium chloride (1) when it is heated in the presence of sodium hydride. We found that the presence of a phenyl substituent has a substantial effect on the direction of the reaction: we isolated two compounds from the reaction mixture in 1.5:1 ratio with overall yield 64%, where the first compound had the structure of the expected 4-phenylpyrrolidine 2 while the other compound, to our surprise, proved to be the tetrahydroazepine 3.…”
mentioning
confidence: 99%
“…With trimethylsilyl azide the product from oxidation of 2,3-dihydro-1H-imidazo- [4,5-c]pyridine 108 forms the 4-azido derivative 109, which is quickly transformed into the tetrazole 110 (yield 46%) [105]. When a mixture of tetrahydropyridine 111 with MnO 2 (a fivefold excess) and malononitrile was kept without heat the hydroxymethylation product 112 was obtained (yield 36.5%) [106,107]. It is assumed that formaldehyde or its imine can be formed from the dinitrile under the reaction conditions and then adds at the multiple bond of the heterocycle.…”
Section: Oxidative Coupling Reactionsmentioning
confidence: 99%
“…102 4-Aryltetrahydropyridines 100a,b were oxidised under more drastic conditions, namely, on boiling in toluene with tenfold excess of MnO 2 . 103,104 Ar = Ph (a, 45%), 4-MeC6H4 (b, 42%).…”
Section: Oxidation Of 4-aryldihydropyridine and -Tetrahydropyridine Dmentioning
confidence: 99%