Iodine(III)‐Mediated Electrophilic Chlorination and Catalytic Nitration of <i>N</i>‐Tosyl Anilines

Patil, Dipak; Gámez-Montaño, Rocı́o; Ordóñez, Mario; Solis-Santos, Melchor; Jiménez‐Halla, J. Óscar C.; Solorio-Alvarado, César R.

doi:10.1002/ejoc.202201295

Cited by 7 publications

(10 citation statements)

References 88 publications

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“…The ortho regioisomer was also calculated. [98] This mechanistic illustration is representative of the chemistry displayed by the PIFA-AlCl 3 combination, which implies a similar behavior for the chlorination of phenols. It is clear that the steps until the formation of 10 A will be the same and from this point onwards the phenol core should be plausibly chlorinated.…”

Section: Chlorination Of N-tosyl Anilinesmentioning

confidence: 74%

“…In 2022, this chlorination process strategy using PIFA-AlCl 3 was extended to N-tosyl anilines. [98] Starting from Standard conditions, the optimal ratio of PIFA and AlCl 3 was found. In this way, several anilines containing groups with different electronic nature were chlorinated in modest to excellent yields.…”

Section: Chlorination Of N-tosyl Anilinesmentioning

confidence: 99%

“…Different naphthols were monoiodinated (92)(93)(94)(95)(96)(97)(98) in good to excellent yields (86-98 %). The addition of more than one iodine atom was not observed for these bis-annular compounds.…”

Section: Iodination With the (Phio) N à Nh 4 I Systemmentioning

confidence: 99%

“…After proving of the broad scope of the iodosylbenzene and aluminum nitrate system in the nitration of phenols, we investigate the application of this development to the nitration of anilines [98] . To our delight, we found this reaction proceeded smoothly, however the tosyl group in the nitrogen of anilines was necessary for the success of the reaction (Scheme 15).…”

Section: The Iodine(iii)‐alx3 System (X=−cl −Br −No2)mentioning

confidence: 99%

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Iodine(III)‐Aluminum or ‐Ammonium Salts for the Oxidative Aromatic Inorganic Functionalization

Chávez‐Rivera,

Navarro‐Santos,

Chacón‐García

et al. 2023

ChemistrySelect

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Strategies for introducing halogens and other inorganic groups in aromatic systems, usually involve non‐general and strong oxidative protocols which resulted in poor functional group compatibility. Iodine(III) reagents have emerged as an excellent alternative for the aromatic inorganic functionalization due to their low toxicity and strong oxidative character. In this context, the synergistic combination of different iodine(III) reagents and aluminum or ammonium salts including AlCl3, AlBr3, Al(NO3)3, NH4Cl, NH4Br and NH4I have recently demonstrated a great versatility for introducing the chlorine, bromine, iodine and nitro groups in aromatic systems, mainly phenols, anilines and some heterocycles. Using these common salts, their anions are softly oxidated by iodine(III) reagents, allowing the in situ formation of non‐described halogenating and nitrating species and in consequence, the introduction of these inorganic groups under an umpolung reactivity as chemical electrophilic synthons.

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Section: Chlorination Of N-tosyl Anilinesmentioning

confidence: 74%

Section: Chlorination Of N-tosyl Anilinesmentioning

confidence: 99%

Section: Iodination With the (Phio) N à Nh 4 I Systemmentioning

confidence: 99%

Section: The Iodine(iii)‐alx3 System (X=−cl −Br −No2)mentioning

confidence: 99%

See 2 more Smart Citations

Iodine(III)‐Aluminum or ‐Ammonium Salts for the Oxidative Aromatic Inorganic Functionalization

Chávez‐Rivera,

Navarro‐Santos,

Chacón‐García

et al. 2023

ChemistrySelect

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“…Organic chemistry is, among the scientific disciplines, the most used tool to obtain treatments for clinical and/or biological affections. This discipline has been evolving with time, increasing the development of compounds with high pharmaceutical interest, using strategies such as metal-catalyzed, [1,2] metalfree [3][4][5][6][7][8][9][10] or natural occurring compounds synthesis and derivatization. [11][12][13] These compounds have been developed with specific goals, such as for the treatment of cancer, [14,15] mycoses, [16] polycystic ovarian, pain, inflammation [17] hyper-glycemia and lastly but not less important: diabetes mellitus.…”

Section: Introductionmentioning

confidence: 99%

Synthesis andin vivoEvaluation of Fluorobenzyl Metformin Derivatives as Potential Drugs in The Diabetes Treatment

Hernández‐Velázquez,

Herrera,

Alba‐Betancourt

et al. 2023

Asian J Org Chem

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Metformin is a versatile, biocompatible, and cheap bis-guanidine used as first response line in the type II diabetes treatment. Since its first human trials (1956) several structural modifications were carried out to increase its activity. However, with this augmented activity, the biological compatibility diminishes, generating serious side effects, such as lactic acidosis. Considering that cytochrome P450 oversees the metformin metabolism and its weakness to eliminate fluorinated metabolites; we envisioned the synthesis of benzyl fluorinated metformin derivatives. In our hypothesis the fluorine atoms can give, by inductive effect, a higher acidity to the hydrogen in the benzylic nitrogen, increasing its solubility. On the other hand, fluorine would give resistance to cP450 allowing the molecule acting longer. Thus, a family of fourteen fluorobenzyl metformins were synthesized and characterized, then an in vitro enzymatic assay with α-amylase was performed to select the five best performing compounds, then an in vivo experiment was carried out with streptozotocin-induced CD1 mice using the selected derivatives. Blood glucose was measured every day. After sacrifice, the lipid profile, serum, and liver γ-glutamyl transferase (GGT) activity determined the biocompatibility. Results showed two compounds (1 L and 1 M) with enhanced activity and higher biocompatibility for blood glucose, lipids metabolism and GGT activity regulation.[a] E.

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Ningalins, Pyrrole‐Bearing Metabolites Isolated from Didemnum spp. Synthesis and MDR‐Reversion Activity in Cancer Therapy

Segura‐Quezada,

Hernández‐Velázquez,

Corrales‐Escobosa

et al. 2024

Chemistry & Biodiversity

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Multi‐Drug Resistance (MDR) is one of the most frequent problems observed in the course of cancer chemotherapy. Cells under treatment, tend to develop survival mechanisms to drug‐action thus generating drug‐resistance. One of the most important mechanism to get it is the over expression of P‐gp glycoprotein, which acts as an efflux‐pump releasing the drug outside of the cancer cell. A strategy for a succesfull treatment consists in the co‐administration of one compound that acts against P‐gp and another which acts against the cell during chemotherapy. Ningalins are pyrrole‐containing naturally occurring compounds isolated mainly from the marine tunicate Didemnum spp and also they are some of the top reversing agents in MDR treatment acting on P‐gp. Considering the relevance displayed for some of these isolated alkaloids or their core as a drug for co‐administration in cancer therapy, all the total synthesis described to date for the members of ningalins family are reviewed herein.

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Iodine(III)‐Mediated Electrophilic Chlorination and Catalytic Nitration of N‐Tosyl Anilines

Cited by 7 publications

References 88 publications

Iodine(III)‐Aluminum or ‐Ammonium Salts for the Oxidative Aromatic Inorganic Functionalization

Iodine(III)‐Aluminum or ‐Ammonium Salts for the Oxidative Aromatic Inorganic Functionalization

Synthesis andin vivoEvaluation of Fluorobenzyl Metformin Derivatives as Potential Drugs in The Diabetes Treatment

Ningalins, Pyrrole‐Bearing Metabolites Isolated from Didemnum spp. Synthesis and MDR‐Reversion Activity in Cancer Therapy

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