Substituted 2-Sulfonamido-5-aminopyridines

Caldwell, William T.; Kornfeld, Edmund C.

doi:10.1021/ja01259a063

Cited by 56 publications

(14 citation statements)

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“…The progress of reactions and the purity of products were monitored by TLC on Silufol UV-254 plates; spots were visualized under UV light. 5-Nitropyridin-2(1H)-one (I) was synthesized as described in [29], and tetrabutylammonium bromide was prepared according to the procedure reported in 1832 [30]. Trimethylsilylacetylene (IIIa), prop-2-yn-1-ol (IIIb), and 2-methylbut-3-yn-2-ol (IIIc) were commercial products (from Fluka) and were used without additional purification.…”

Section: Methodsmentioning

confidence: 99%

Nitropyridines: X. Palladium-catalyzed cross-coupling of 2-bromo-5-nitropyridine with terminal acetylenes

et al. 2010

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Substituted 5-nitro-2-ethynylpyridines were synthesized by the Sonogashira reaction of 2-bromo-5-5-nitropyridine with terminal acetylenes. Desilylation, oxidative decarbonylation, and the retro-Favorskii reaction of the cross-coupling products of 2-bromo-5-nitropyridine with trimethylsilylacetylene, prop-2-ynyl alcohol, and 2-methylbut-3-yn-2-ol, respectively, gave 2-ethynyl-5-nitropyridine. The hydration of 2-ethynyl-5-nitropyridine and 5-nitro-2-(phenylethynyl)pyridine according to Kucherov afforded 2-acetyl-5-nitropyridine and 5-nitro-2-phenacylpyridine, respectively.

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Section: Methodsmentioning

confidence: 99%

Nitropyridines: X. Palladium-catalyzed cross-coupling of 2-bromo-5-nitropyridine with terminal acetylenes

et al. 2010

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“…Bu bileşiğin sentezinde ise Caldwell ve Korngeld'in yöntemi uygulanmıştır (5). Yöntemin esası, 2-aminopiridin bileşiğinin sülfürük asit ve nitrik asit karışımı ile nitrolanmasıdır.…”

Section: Materyalunclassified

“…Birbirinden ayrılma için uygulanan işlem son derece uzun ve karışıktır. Caldwell ve Korngeld'in sentez yönteminde ise su buharı distilasyonu uygulanarak 2-amino -3-nitropiridin saf olarak elde edilebilmiştir (5 2,3-Diaminopiridin Sentez Yöntemi: Petrow ve Saper'in 5-azakinoksalin ve 4-azabenzimidazol sentezi için kullandıkları 2,3-diaminopiridin sentez yöntemi bu çalışmada da uygulanmıştır (7). Buna göre, 2-amino -3-nitropiridin metanol-su karışımında indirgenmiş demir ve hidroklorik asit karışımı ile hidrojene edildikten sonra alkali ile çöktürülüp benzen ile tüketilmiştir.…”

Section: Materyalunclassified

3H-İmidazo (4,5-b) ve (4,5-c) Piridinlerin 2- Alkil Sübstitüe Türevlerinin Sentez ve Yapı Açıklamaları

Özden¹

1981

Ankara Universitesi Eczacilik Fakultesi Dergisi

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Bu noktadan hareketle, literatürde yapılan incelemelerde, imidazopiridin türevi bileşikler üzerinde sistematik yapı değişikliği araştırmalarının az olduğu ve özellikle 2 no. lu konumda bulunan grupların belirli bir düzen içinde ele alınmadığı dikkati çekmektedir. Ayrıca, sentezi yapılan imidazopiridin türevlerinde biyosid, virusid, antienflamatuvar, analjezik, antihelmentik, antikarsinojenik, antitümör, antihistaminik gibi çeşitli farmakolojik etkiler gözlenmiştir. Bu etkilerin ortaya çıkışında özellikle 2 no. lu konumda yapılan sübstitüsyonlarm önemli bir rol oynadığı görülmektedir.

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“…hydrochloric acid permits unstable and azinesulfonyl chlorides 8,9,16,18,19 to be isolated. 8,9,16,18,19 It is worth noting that structural modification may affect the stability of and -azinesulfonyl halides, as was exemplified for 5-acetylamino-2-pyridinesulfonyl chloride, 15 for tetrachloro-4-pyridinesulfonyl chloride, 17 and even for 2-pyrimidinesulfonyl fluoride. 8,9,16,18,19 It is worth noting that structural modification may affect the stability of and -azinesulfonyl halides, as was exemplified for 5-acetylamino-2-pyridinesulfonyl chloride, 15 for tetrachloro-4-pyridinesulfonyl chloride, 17 and even for 2-pyrimidinesulfonyl fluoride.…”

Section: Introductionmentioning

confidence: 99%

From 2,3-, 2,6-, 3,4- and 4,6-Dichloroquinolines to Isomeric Chloroquinolinesulfonyl Chlorides

Marciniec¹,

Maślankiewicz²

2010

HETEROCYCLES

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The action of sodium methanethiolate (in boiling DMF) on x,ydichloroquinolines (1) (x=3 or 6, y=2 or 4) occured via chlorine ipso-substitution followed by methanethiolato-S-demethylation to yield x,y-quinolinedithiolates 2A which were: i) subjected to S-methylation, ii) oxidatively chlorinated to y-chlorox-quinolinesulfonyl chlorides (5). Oxidative chlorination of y,y'-bis(x-chloroquinolinyl) disulfides (7) led to x-chloro-y-quinolinesulfonyl chlorides (8) accompanied by x,y-dichloroquinolines (1). Both quinolinesulfonyl chlorides 5 and 8 were efficiently converted to the corresponding quinolinesulfonamides 6 and 9.

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Substituted 2-Sulfonamido-5-aminopyridines

Cited by 56 publications

References 0 publications

Nitropyridines: X. Palladium-catalyzed cross-coupling of 2-bromo-5-nitropyridine with terminal acetylenes

Nitropyridines: X. Palladium-catalyzed cross-coupling of 2-bromo-5-nitropyridine with terminal acetylenes

3H-İmidazo (4,5-b) ve (4,5-c) Piridinlerin 2- Alkil Sübstitüe Türevlerinin Sentez ve Yapı Açıklamaları

From 2,3-, 2,6-, 3,4- and 4,6-Dichloroquinolines to Isomeric Chloroquinolinesulfonyl Chlorides

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