Facile and selective synthesis of chloronicotinaldehydes by the Vilsmeier reaction

Gangadasu, B.; Narender, P.; Kumar, Sanjeev; Ravinder, M.; Rao, B. Appa; Ramesh, C.; Raju, B. China; Rao, V. Jayathirtha

doi:10.1016/j.tet.2006.06.026

Cited by 56 publications

(24 citation statements)

References 25 publications

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“…A pyridine aldehyde (3a-c) was reacted with a benzene-1,2-diamine or pyridine-2, 3-diamine (4a-f) in the presence of CAN/H 2 O 2 to give 2-(pyridin-3-yl)-1H-benzo[d]imidazoles or 2-(pyridin-3-yl)-3H-imidazo [4,5-b]pyridine derivatives, respectively (5a-5k), in good yield and purity. The pyridine aldehyde intermediates (3a-c) were prepared directly or via enamide formation starting from pent-3-en-2-one oxime, 4-phenyl-3-butene-2-one-oxime, or methyl 2-acetamidoacrylate (Table 1) [28][29][30][31].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of antibacterial 2-(pyridin-3-yl)-1H-benzo[d]imidazoles and 2-(pyridin-3-yl)-3H-imidazo[4,5-b]pyridine derivatives

Mallemula

Sanghai²,

Himabindu

et al. 2013

Res Chem Intermed

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The increasing clinical importance of drug-resistant fungal and bacterial pathogens has stimulated microbiological research into and development of new antimicrobial agents. Hence, in this study, we synthesized novel series of 2-(pyridin-3-yl)-1H-benzo[d]imidazoles and 2-(pyridin-3-yl)-3H-imidazo[4,5-b]pyridine derivatives. The structures of the compounds were confirmed by spectral and CHN analysis. The compounds were examined for in-vitro antimicrobial activity against Gram-positive bacteria (Staphylococcus aureus and Bacillus subtilis), Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa), and the fungus Candida albicans.

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Section: Resultsmentioning

confidence: 99%

Synthesis and characterization of antibacterial 2-(pyridin-3-yl)-1H-benzo[d]imidazoles and 2-(pyridin-3-yl)-3H-imidazo[4,5-b]pyridine derivatives

Mallemula

Sanghai²,

Himabindu

et al. 2013

Res Chem Intermed

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“…[135,136] In the same context, calcium chloride is able to act as a Lewis base catalyst in the reaction of (RO) 2 POH with isocyanates 120 (or isothio-analogue) producing the carbamoyl or thiocarbamoyl phosphonic esters 121. [137][138][139] Other catalysts such as pyridinium halides [PyH] + X -were also applied in similar reactions. [140,141] Failla and Finochiaro reported that carbanilino-phosphonates 123 were obtained from the reaction of α-hydroxyphosphonates 122 (derived from the parent aldehydes and (RO) 2 POH) with phenylisocyanates in the presence of tin octanoate (Scheme 52).…”

Section: Reactions With Isocyanates and Isothiocyanatesmentioning

confidence: 99%

Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates

Abdou

Barghash

Bekheit

2015

Synthetic Communications

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In this study, we report recent investigations of the chemical reactivity of alkyl phosphites mainly trialkyl and dialkyl phosphites with molecules containing different nitrogen-containing compounds reported by us and other research groups over the last twenty five years. Earlier leader important reports were also considered. The reviewed investigations in this article are customized, only according to the type of the nitrogenfunctional groups: [amines (primary, secondary, and tertiary amines), imines, amides, thioamides, nitriles, isocyanates, isothiocyanates, oximes, hydrazones, diazo, and azides]and not according to the site of attack or the final products. Furthermore, the present review article focuses on the synthesis of α-amino-, β-amino-and/or enaminophosphonates. These compounds occupy an important role in pharmaceutical chemistry.2 GRAPHICAL ABSTRACT:

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“…Jayathirtha Rao 等 [46] 用取代的 N-乙烯基乙酰胺, 在三氯氧磷或三光气、二光气与 DMF 复合成的 Vilsmeier 试剂作用下, 合成了相应取代的 2-氯-3-吡啶甲醛衍生物. 其反应如 Eq.…”

Section: 另外除双键与醇羟基形成 α-烯醇或 β-烯醇与unclassified

Application of Vilsmeier Reagents in Cyclization in Recent Years

Qian¹,

Zhou²,

Zhan³

et al. 2012

Chin. J. Org. Chem.

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The Vilsmeier-Hack reaction has historically been a topic of great interest to organic chemists, and it continues to attract considerable attention. The Vilsmeier-Hack reaction provides a facile entry into large numbers of aromatic and heteroaromatic systems. Vilsmeier reagents generated from amides and halides have been found to be very important in organic synthesis. Acylation, chlorination, chloroformylation, aromatization, rearrangement, dehydration and cyclization are the most reactions of Vilsmeier reagents. The application of Vilsmeier reagents in cyclization is introduced.

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Facile and selective synthesis of chloronicotinaldehydes by the Vilsmeier reaction

Cited by 56 publications

References 25 publications

Synthesis and characterization of antibacterial 2-(pyridin-3-yl)-1H-benzo[d]imidazoles and 2-(pyridin-3-yl)-3H-imidazo[4,5-b]pyridine derivatives

Synthesis and characterization of antibacterial 2-(pyridin-3-yl)-1H-benzo[d]imidazoles and 2-(pyridin-3-yl)-3H-imidazo[4,5-b]pyridine derivatives

Investigations of the Chemistry of Alkyl Phosphites Toward Nitrogen-Containing Compounds: Efficient Approaches to α-Amino-, β-Amino-, and/or Enaminophosphonates

Application of Vilsmeier Reagents in Cyclization in Recent Years

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