Regioselective ketalization (dioxane vs dioxolane) study of internal diastereomeric 1,2,3-triol systems obtained from d-pentoses

Donthulachitti, Chiranjeevi; Ramakrishna, Yelukala; Shekunti, Ravikumar; Neella, Chandra Kiran

doi:10.1016/j.rechem.2022.100341

Cited by 6 publications

(2 citation statements)

References 14 publications

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“…Previously this reagent was prepared from our laboratory by reacting benzoylchloride with DMAP in ethylacetate which was employed for regioselective monobenzoylation. [45] Gratifyingly, when 3.3 eq. of reagent 1 and 3.3 eq.…”

Section: Resultsmentioning

confidence: 99%

N‐Benzoyl‐4‐dimethylaminopyridinium Chloride: A Lewis Base Adduct for Efficient Poly and Monobenzoylation

et al. 2022

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N-benzoyl-4-dimethylaminopyridinium chloride [DMAPBz] + Cl À was efficiently employed for polybenzoylation of triols and tetrols without epimerization and elimination products. This Lewis base adduct has also been employed for regioselective monobenzoylation of polyols obtained from D-pentoses. Fur-ther an eco-friendly monobenzoylation of phenols, amines and alcohols was achieved in water as a solvent without using a base and chromatographic purification of the products. Chemoselective monobenzoylation and recovery of the DMAP is an added advantage of our protocol.

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Section: Resultsmentioning

confidence: 99%

N‐Benzoyl‐4‐dimethylaminopyridinium Chloride: A Lewis Base Adduct for Efficient Poly and Monobenzoylation

et al. 2022

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“…[21] Though the thorough structural and mechanistic investigations of N-acetylpyridinum ions were established, their synthetic applications as direct reagents were never studied before our group endeavoured into it wherein well de ned synthetic procedures were developed for isolation of Transient species of DMAP and also their structures are unambiguously corroborated from all the spectra. Inspired by our results on DMAP [22][23][24][25][26][27][28][29] , we wished for exploring the structures and chemical properties of transient species of DBU which is not attempted so far. Herein we report the synthesis, unambiguous structural characterization and their synthetic applications as green reagents of transient species of DBU as a super-nucleophilic base [30] as this area of DBU is not explored so far.…”

Section: Introductionmentioning

confidence: 99%

Preparation, Isolation and Structural Characterization of Transient Species of DBU. Their Application as Green Reagents

Thangalipalli,

Bandalla,

Vadala

et al. 2024

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A state of the art synthesis and isolation procedure is developed for 17 different transient species of DBU. The structure of these transient species, which are thoroughly confirmed from various spectral data, is different from their parent compound DBU and provides emphatic support in favor of formation of transient species in various DBU catalyzed reactions. DFT studies of N-sulphonylTransient species of DBU has given a new insight of an alternate transient species in addition to the normal species which provides a new scope for further investigation. The applications of three Transient species as direct reagents for base free functionalizations are also documented. They can be directly employed as Eco-friendly reagents in water as solvent. The Lewis base can be recovered and reused for the preparation of Transient species after the reaction. The influence of N-substituent on the chemical shift of these transient species also documented.

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N‐Iodo‐4‐N,N‐Dimethylaminopyridinium Iodide; A New Green Iodination Reagent for Regioselective Mono and Di Iodination of Phenols and Anilines in Water with Good E‐Factor

2023

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A new Green Iodinating reagent, N‐Iodo‐4‐N,N‐Dimethylaminopyridinium Iodide, is identified, prepared and the structure is unambiguously established. The reagent is employed for metal/coreagent free regioselective mono and also diiodination of phenols and anilines. This is the first report wherein both phenol and aniline regioselectively produced only ortho monoiodo derivatives. Chemoselectivity and nucleo‐selectivity were also gained from this methodology. Our procedure is an Eco‐friendly one due to Good E‐factor (0.27), recovery and recycling of DMAP, Non‐chromatography purification of products and water as solvent.

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Regioselective ketalization (dioxane vs dioxolane) study of internal diastereomeric 1,2,3-triol systems obtained from d-pentoses

Cited by 6 publications

References 14 publications

N‐Benzoyl‐4‐dimethylaminopyridinium Chloride: A Lewis Base Adduct for Efficient Poly and Monobenzoylation

N‐Benzoyl‐4‐dimethylaminopyridinium Chloride: A Lewis Base Adduct for Efficient Poly and Monobenzoylation

Preparation, Isolation and Structural Characterization of Transient Species of DBU. Their Application as Green Reagents

N‐Iodo‐4‐N,N‐Dimethylaminopyridinium Iodide; A New Green Iodination Reagent for Regioselective Mono and Di Iodination of Phenols and Anilines in Water with Good E‐Factor

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