2,4,6-Trichloro-1,3,5-triazine and N,N′-dimethylformamide as an effective Vilsmeier–Haack reagent for the synthesis of 2-chloro-3-formyl quinolines from acetanilides

Venkanna, P.; Rajanna, K. C.; Kumar, M. Satish; Ansari, Mohd Bismillah; Ali, M. M.

doi:10.1016/j.tetlet.2015.07.056

Cited by 22 publications

(11 citation statements)

References 61 publications

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“…The synthetic route of compounds 6 is outlined in Scheme . According to the novel synthetic method, compound 2 was synthesized from 4‐methoxy‐benzenamin 1 by treatment with acetic anhydride in dry DCM.…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, and cytotoxic evaluation of novel furo[2,3‐b]quinoline derivatives

Wang

Shi

et al. 2018

Chem Biol Drug Des

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A number of novel furo[2,3-b]quinoline derivatives were designed and synthesized by introducing benzyl ether, benzoate, and benzenesulfonate to 6-position of furo[2,3-b]quinoline and their chemical structures were confirmed by ESI-MS, H NMR, and C NMR spectra. All target compounds were evaluated in vitro against four human cancer cell lines (HCT-116, MCF-7, U2OS, and A549) by MTT method. Cytotoxic assay showed that compounds 8a, 8e, 10a, 10b, and 10c exhibited more potent cytotoxicities compared to 2-bromine-6-hydroxy-furo-[2,3-b]quinoline (7). Compound 10c exhibited higher antiproliferative activity (IC values ranging from 4.32 to 24.96 μm) against four human cancer cell lines (HCT-116, MCF-7, U2OS, and A549) and weak cytotoxicity on normal cell HL-7702, which suggested that 10c might be an ideal anticancer candidate. Compounds 8a, 10a, 10b showed good selectivities to MCF-7 and HCT-116, which could be considered as ideal selective candidates for further study. The SARs showed that the introduction of the benzyl ether and benzenesulfonate could significantly improve cytotoxicities, while the benzoate failed to enhance potency obviously.

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Section: Resultsmentioning

confidence: 99%

Design, synthesis, and cytotoxic evaluation of novel furo[2,3‐b]quinoline derivatives

Wang

Shi

et al. 2018

Chem Biol Drug Des

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“…These observations are largely similar to those in our earlier reports on the formation of TCTA/DMF and TCCA/DMF adducts, respectively. 29,30 The chloromethyleniminum cation thus formed reacts with the acetanilide to afford 3-acetyl-2-chloroquinolines. (Spectroscopic data for the isolated 3-acetyl-2-chloroquinolines are given in supplementary data.)…”

Section: Letter Syn Lettmentioning

confidence: 99%

“…Efforts have been made to avoid the use of oxychlorides by replacing them with 2,4,6-trichlorotriazine (cyanuric chloride, TCTA) 17,18 to give the corresponding DMF adducts as alternative Vilsmeier-Haack reagents. Symmetrical 1,3,5-triazine derivatives have also been used to promote transformations such as Friedel-Crafts acylations, Beckman rearrangements, Lossen rearrangements, carboxylic-acid activations, and Swern oxidations.…”

mentioning

confidence: 99%

Symmetrical Trichlorotriazine Derivatives as Efficient Reagents for One-Pot Synthesis of 3-Acetyl-2-chloroquinolines from Acetanilides under Vilsmeier–Haack Conditions

Muddam

Venkanna

Venkateswarlu

et al. 2017

Synlett

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Symmetrical trichlorotriazine derivatives such as 2,4,6-trichloro-1,3,5-triazine and trichloroisocyanuric acid were explored as Vilsmeier–Haack type reagents in the presence of N,N-dimethylacetamide for the effective synthesis of 3-acetyl-2-chloroquinolines from acetanilides. Ultrasonication led to shorter reaction times than conventional heating and gave yields comparable to those obtained under reflux conditions.

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“…o ‐Halobenzaldehydes are largely available and have been extensively used in the synthesis of heterocycles. In particular, 2‐chloro‐3‐quinolinecarboxaldehyde, which can be prepared easily from acetanilide by using either POCl 3 /DMF or 2,4,6‐trichloro‐1,3,5‐triazine/DMF as the Vilsmeier–Haack reagent, has recently emerged as an important building block for organic synthesis (Figure ). Recently, α‐bromocinnamaldehyde, which is the α‐bromination product of cinnamaldehyde with N ‐bromosuccinimide, has also been used as a unique synthon and can be considered as a variation of aromatic aldo‐halide bifunctional building block as well.…”

Section: Benzaldo‐x Bifunctional Building Blocks and Their Heterocyclmentioning

confidence: 99%

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

Ravichandiran

Lai

2016

The Chemical Record

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Compounds containing oxygen, nitrogen, or sulfur atoms inside the rings are attracting much attention and interest due to their biological importance. In recent years, several methods for the synthesis of such molecules have been reported by using aldo-X bifunctional building blocks (AXB3 s) as substrates; these are a wide class of organic molecules that contain at least two reactive sites, among them, one aldehyde, acetal, or semiacetal group was involved. Because of the multiple reactivities, AXB3 s are widely used in the one-pot synthesis of biologically important heterocycles. This review summarizes the synthesis of important heterocycles by using AXB3 s as pivotal components in establishing multicomponent reactions, tandem reactions, and so forth. In many cases, the established reaction systems with AXB3 s were characterized by some green properties, such as easy access to the substrate, mild and environmentally benign conditions, and wide scope of the substrate.

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2,4,6-Trichloro-1,3,5-triazine and N,N′-dimethylformamide as an effective Vilsmeier–Haack reagent for the synthesis of 2-chloro-3-formyl quinolines from acetanilides

Cited by 22 publications

References 61 publications

Design, synthesis, and cytotoxic evaluation of novel furo[2,3‐b]quinoline derivatives

Design, synthesis, and cytotoxic evaluation of novel furo[2,3‐b]quinoline derivatives

Symmetrical Trichlorotriazine Derivatives as Efficient Reagents for One-Pot Synthesis of 3-Acetyl-2-chloroquinolines from Acetanilides under Vilsmeier–Haack Conditions

Aldo‐X Bifunctional Building Blocks for the Synthesis of Heterocycles

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