NaIO4/KI/NaCl: a new reagent system for iodination of activated aromatics through in situ generation of iodine monochloride

Emmanuvel, Lourdusamy; Shukla, Ravi; Sudalai, Arumugam; Suryavanshi, Gurunath; Sivaram, Swaminathan

doi:10.1016/j.tetlet.2006.05.062

Cited by 54 publications

(26 citation statements)

References 29 publications

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“…The use of polyphosphoric acid (PPA) in cyclisation reactions is well known in the literature, and has been used to form a large variety of ring structures [15]. Iodination of 3 could then be realised by utilising the rich iodination literature available [16–17]. …”

Section: Resultsmentioning

confidence: 99%

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

Chisholm¹,

Zhou²,

Pohl³

et al. 2016

Beilstein J. Org. Chem.

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SummaryThe synthesis of novel tetrahydroquinolines (THQ) and dihydroquinolines (DHQ) are reported using three practical, scalable synthetic approaches to access highly lipophilic analogues bearing a 6-iodo substituent, each with a different means of cyclisation. A versatile and stable quinolin-2-one intermediate was identified, which could be reduced to the corresponding THQ with borane reagents, or to the DHQ with diisobutylaluminium hydride via a novel elimination that is more favourable at higher temperatures. Coupling these strongly electron-donating scaffolds to electron-accepting moieties caused the resulting structures to exhibit strong fluorescence.

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Section: Resultsmentioning

confidence: 99%

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

Chisholm¹,

Zhou²,

Pohl³

et al. 2016

Beilstein J. Org. Chem.

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“…The most used are: I 2 AF 3 CCOOAg, I 2 AHgO, I 2 AAg 2 SO 4 , I 2 ACr 2 O 3 , I 2 APb(OAc) 2 , I 2 ATlOAc, I 2 AKIAHg(OAc) 2 , I 2 A(Bu 4 N) 2 S 2 O 8 , I 2 ANa 2 S 2 O 8 , N-iodosuccinimide (NIS), NISACF 3 SO 3 H, ICl, NH 4 I-oxone, NaOClANaI, etc. [12,13]. In all these cases the iodine or iodine-containing source is used in a combination with a strong activating agent in order to create an efficient iodinium donating system.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, and crystal structure of 2-iodo-3,4,5-trimethoxybenzoic acid

Kolev

Petrova

Nikolova

et al. 2013

Journal of Molecular Structure

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“…We have developed a two‐step procedure, not reported for the preparation of carboxylic acid 29 , which involved iodination followed by Sandmeyer's reaction for chlorination. Iodination of anthranilic acid 27 was achieved using literature procedure and this furnished the iodinated anthranilic acid 28 in good yields. The diazotization reaction followed by replacement of diazonium group with chloro‐group using CuCl gave the desired carboxylic acid 29 in good yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Benzyl C‐Analogues of Dapagliflozin as Potential SGLT2 Inhibitors

et al. 2020

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Sodium‐glucose co‐transporter (SGLT) inhibitors are a novel class of therapeutic agents for the treatment of type 2 diabetes based on blocking of renal reabsorption of glucose. Dapagliflozin, a C‐aryl glucoside, has emerged as a successful drug in the market based on this concept. We have synthesized hitherto unreported C‐benzyl glucoside analogues of Dapagliflozin carrying the same aglycon present in the drug. The synthetic strategy involves in situ generation of functionalized arylmagnesium bromide with Weinreb‐amide (WA) functionality for the first time, and addition on to the 1‐β‐formyl‐2,3,4,6‐tetra‐O‐benzyl‐D‐glucopyranoside for the synthesis of a C‐benzyl glucoside building block 16. The WA functionality therein enabled variation in the nature of the distal ring of biarylmethane aglycon for convenient access to other analogues. All the new compounds were screened for their sodium‐glucose co‐transporters (SGLT1 and SGLT2) inhibition activity using cell‐based nonradioactive fluorescence glucose uptake assay. Among them, 14 with IC50: 0.64 nm emerged as the most potent SGLT2 inhibitor with the best selectivity for inhibition of SGLT2 (IC50:0.64 nm) over SGLT1 (IC50: 500 nm) as compare to Dapagliflozin. On the other hand, compound 15a exhibited moderate selectivity for inhibition of SGLT2 (IC50: 4.94 nm) over SGLT1 (IC50: 68.46 nm). These results presented herein amply demonstrate the promise of C‐benzyl analogues of Dapagliflozin as novel SGLT2 inhibitors for future investigations.

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NaIO4/KI/NaCl: a new reagent system for iodination of activated aromatics through in situ generation of iodine monochloride

Cited by 54 publications

References 29 publications

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

Synthesis, characterization, and crystal structure of 2-iodo-3,4,5-trimethoxybenzoic acid

Synthesis of Benzyl C‐Analogues of Dapagliflozin as Potential SGLT2 Inhibitors

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