Combination of NH2OH·HCl and NaIO4: a new and mild reagent for the synthesis of vicinal diiodo carbonyl compounds

Santra, Sougata; Kundu, Shrishnu Kumar; Ghosal, Nirnita Chakraborty; Chatterjee, Rana; Mahato, Sachinta; Khalymbadzha, Igor A.; Zyryanov, Grigory V.; Hajra, Alakananda; Majee, Adinath

doi:10.24820/ark.5550190.p009.698

Cited by 4 publications

(3 citation statements)

References 25 publications

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“…The reaction mechanism has not been well investigated. Based on our previous works, literature, and the present observation the reaction path may be two types (Scheme ). In path I the ring opening of alcohol, which is the common product of epoxide, further undergoes oxidation.…”

Section: Methodsmentioning

confidence: 67%

“…In our first observation we have observed a clean and controlled oxidation of alcohols to carbonyl compounds under mild conditions using NH 2 OH⋅HCl and NaIO 4 . In case of the both second and third we have observed the addition of simple iodine from the same reagents under similar reaction conditions. Accordingly as a model reaction we have taken the epoxy carbonyl compound ( 1 a ) prepared from simple chalcone to expose our developed reagent combination of NH 2 OH⋅HCl and NaIO 4 .…”

Section: Methodsmentioning

confidence: 69%

“…There is no other approach in literature for its synthesis using different precursor involving other organic functionalities. We are actively engaged to develop new reagents and reaction conditions in organic synthesis and as outcome recently we have developed a new reagent combination (NH 2 OH⋅HCl and NaIO 4 ) for selective oxidation of alcohols to corresponding carbonyl compounds, synthesis of β ‐iodo‐ β′ ‐hydroxy ethers, β ‐iodo ethers, β ‐iodohydrin, and β ‐iodo acetoxy compounds and 1,2‐diiodo carbonyl compounds . Our developed methodologies are very mild and efficient.…”

Section: Methodsmentioning

confidence: 99%

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A Domino Approach for the Synthesis of α‐Iodo‐β‐dicarbonyl Compounds from α‐Epoxycarbonyls

et al. 2017

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A series of a-iodo-b-dicarbonyl compounds have been synthesized from a-epoxycarbonyl compounds through a consecutive reaction by ring opening of epoxide followed by the oxidation in presence of NH 2 OH·HCl and NaIO 4 . To the best of our knowledge, this is the first time report for the use of aepoxycarbonyls as a key starting material for the synthesis of aiodo-b-dicarbonyl compounds. Various functional groups are well tolerated under the present reaction conditions. The epoxy carbonyl compound containing alkyl part is also effective for this conversion. The reactions were carried out in open atmosphere and are not sensitive to air and moisture. All of the synthesized compounds have been characterized by spectral and analytical data. The potential synthetic applicability of this method was investigated on a gram scale using the model reaction. The advantages of the present method are operational simplicity, short reaction time, general applicability, good tolerance to scale-up synthesis, as well as readily available reagents. A plausible mechanism has been proposed on the basis of an intermediate isolated from the reaction mixture.The synthetic pursuit of iodo-containing compounds is very useful conversion due to their extensive applications in organic synthesis, in the pharmaceutical industry, and in materials science. [1] In organic synthesis a-halogenation of 1,3-dicarbonyl compounds is an important task as these are used as versatile intermediates in various synthetic organic transformations. [2] Since the monosubstituted product is always accompanied by a small amount of disubstituted product; a-monohalogenation of 1,3-dicarbonyl compounds attracted more attention and is considered as a challenging problem. Several methods are available in literature for a-monohalogenation (Br, Cl, I) of 1,3-dicarbonyl compounds [3] but due to the poor electrophilic strength of iodine, simple iodination of 1,3-dicarbonyl compounds is difficult and requires the presence of an activating agent in order to produce a strongly electrophilic I + species. Methods involve mainly the modification of N-iodosuccinimide, [3a-c] use of HIO 4 /Al 2 O 3 , [3d] using elemental iodine and oxone. [3e] In addition, other reagents have been less investigated. [3f] So, all the reported syntheses of a-monohalogenated-1,3-dicarbonyl compounds involve the simple conversion of 1,3-dicarbonyl compounds to its a-halo-derivatives (Scheme 1a).There is no other approach in literature for its synthesis using different precursor involving other organic functionalities. We are actively engaged to develop new reagents and reaction conditions in organic synthesis [4] and as outcome recently we have developed a new reagent combination (NH 2 OH·HCl and NaIO 4 ) for selective oxidation of alcohols to corresponding carbonyl compounds, [5] synthesis of b-iodo-b'-hydroxy ethers, b-iodo ethers, b-iodohydrin, and b-iodo acetoxy compounds [6] and 1,2-diiodo carbonyl compounds. [7] Our developed methodologies [4][5][6] are very mild and efficient. Inspired by the...

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Section: Methodsmentioning

confidence: 67%

Section: Methodsmentioning

confidence: 69%

Section: Methodsmentioning

confidence: 99%

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A Domino Approach for the Synthesis of α‐Iodo‐β‐dicarbonyl Compounds from α‐Epoxycarbonyls

et al. 2017

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Mild, Efficient and Metal‐Free Strategies for Direct Diamination of α, β‐Unsaturated Ketones Using Different Iodine Sources

et al. 2021

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Reaction of α, β‐unsaturated ketone (chalcone) and secondary amine leads to direct diamination of chalcone by dehydrogenation and forming two C−N bonds. This diamination reaction of chalcones with morpholine has been carried out through two effective protocols. The use of N‐iodosuccinimide (NIS) in tetrahydrofuran solvent in one strategy, while the combination of NH2OH ⋅ HCl and NaIO4 in dichloromethane solvent in another are very effective and work at room temperature. No other additives are required for this conversion. Mild and metal free conditions, simple operation technique, good to excellent yields are the notable advantages of both these protocols.

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A practicable synthesis of 2,3-disubstituted 1,4-dioxanes bearing a carbonyl functionality from α,β-unsaturated ketones using the Williamson strategy

Santra

Khalymbadzha

et al. 2021

Org. Biomol. Chem.

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Combination of NH2OH·HCl and NaIO4: a new and mild reagent for the synthesis of vicinal diiodo carbonyl compounds

Cited by 4 publications

References 25 publications

A Domino Approach for the Synthesis of α‐Iodo‐β‐dicarbonyl Compounds from α‐Epoxycarbonyls

A Domino Approach for the Synthesis of α‐Iodo‐β‐dicarbonyl Compounds from α‐Epoxycarbonyls

Mild, Efficient and Metal‐Free Strategies for Direct Diamination of α, β‐Unsaturated Ketones Using Different Iodine Sources

A practicable synthesis of 2,3-disubstituted 1,4-dioxanes bearing a carbonyl functionality from α,β-unsaturated ketones using the Williamson strategy

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