1963
DOI: 10.1021/jo01037a026
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A Comparison of Methods for the Preparation of 2- and 4-Styrylpyridines1

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Cited by 63 publications
(33 citation statements)
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“…Com pound 7e and new dichloro substituted 4 styrylpyridine 7f were synthesized by the condensation of 4 picoline and the corresponding substituted benzaldehyde in acidic con ditions by analogy with the synthesis of related compounds 7c,d,g. 24 Analogs of dyes 1 containing different substitu ents in the benzene fragment instead of the crown ether moiety, viz., iodides 2a,b and perchlorates 3a,c-g and 5, were synthesized by the treatment of 4 styrylpyridines 7a-g and 2 styrylbenzothiazole 8 with ethyl iodide or ethyl tosylate followed by the ionic exchange with HClO 4 in the case of the preparation of perchlorate salts. Com pound 7b containing the NMe 2 substituent in the ben zene fragment was subjected to the double N alkylation by fusion with an excess of EtOTs followed by the trans formation into the perchlorate salt, which resulted in the formation of dicationic dye 3h instead of the expected monocationic dye 3b.…”
Section: Resultsmentioning
confidence: 99%
“…Com pound 7e and new dichloro substituted 4 styrylpyridine 7f were synthesized by the condensation of 4 picoline and the corresponding substituted benzaldehyde in acidic con ditions by analogy with the synthesis of related compounds 7c,d,g. 24 Analogs of dyes 1 containing different substitu ents in the benzene fragment instead of the crown ether moiety, viz., iodides 2a,b and perchlorates 3a,c-g and 5, were synthesized by the treatment of 4 styrylpyridines 7a-g and 2 styrylbenzothiazole 8 with ethyl iodide or ethyl tosylate followed by the ionic exchange with HClO 4 in the case of the preparation of perchlorate salts. Com pound 7b containing the NMe 2 substituent in the ben zene fragment was subjected to the double N alkylation by fusion with an excess of EtOTs followed by the trans formation into the perchlorate salt, which resulted in the formation of dicationic dye 3h instead of the expected monocationic dye 3b.…”
Section: Resultsmentioning
confidence: 99%
“…The compounds N-methyl-4-picolinium iodide [25] ([mepic + ]I), 4-(dimethylaminophenyl)pyridine´0.15H 2 O, [11] 4-(4-dimethylaminophenyl)-N-methylpyridinium iodide [12] ([1]I), 4-(4-dimethylaminophenyl)-N-phenylpyridinium chloride [12] ([2]Cl), 4-(4-dimethylaminophenyl)-N-(2,4-dinitrophenyl)pyridinium chloride´0.8H 2 O [12] ([3]Cl´0.8H 2 O), trans-4¢-(dimethylamino)-N-methyl-4-stilbazolium hexafluorophosphate [7] ([5]PF 6 ), trans-4¢-(dimethylamino)-N-phenyl-4-stilbazolium hexafluorophosphate [7] ([6]PF 6 ), trans-4¢-(dimethylamino)-N-(2,4-dinitrophenyl)-4-stilbazolium hexafluorophosphate [7] ([7]PF 6 ), trans-4¢-(dimethylamino)-N-(2-pyrimidyl)-4-stilbazolium hexafluorophosphate [7] ([8]PF 6 ), trans-4¢-methoxy-N-methyl-4-stilbazolium iodide [26] ([13]I), N-phenyl-4-picolinium chloride´1.25H 2 O [7] ([ppic + ]Cl´1.25H 2 O), trans-4¢-methoxy-4-stilbazole [27] and 4-picolyltriphenylphosphonium chloride [28] were prepared according to published procedures. [ and 2-chloropyrimidine (573 mg, 5.00 mmol) was heated quickly to 80 C, forming a red melt.…”
Section: Methodsmentioning
confidence: 99%
“…The widely known method of preparation of olefi n derivatives is Wittig reaction [13,14] consisting in the reaction of phosphorus ylides with carbonyl compounds. The 3-methoxybenzyltriphenylphosphonium salt obtained in the fi rst stage was further subjected to α-deprotonation under the treatment with a strong base (NaOH), and thus formed phosphonium ylide reacted with quinoline-2-carbaldehyde giving 2-styrylquinoline (II) in 74% yield (Scheme 3).…”
mentioning
confidence: 99%