<i>N</i>‐Bromosuccinimide‐Mediated Thiocyanation of Cyclohexene‐Fused Isoxazoline <i>N</i>‐Oxides

Ichake, Sachin S.; Rajawinslin, R. R.; Kavala, Veerababurao; Villuri, Bharath Kumar; Yang, Haiying; Kuo, Chun Wei; Yao, Ching Fa

doi:10.1002/ajoc.201500453

Cited by 7 publications

(3 citation statements)

References 62 publications

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“…Analogous NBS-mediated transformation in the presence of NH4SCN results in a formation of SCN-substituted cyclohexenes 28. 24 In both cases, the reaction proceeds via an intermediate formation of nitroso compounds 26 (Scheme 9).…”

Section: Scheme 7 Cyclization Of Gem-bromonitromethanes 19 With Alkenesmentioning

confidence: 99%

“…Analogous NBS-mediated transformation in the presence of NH 4 SCN resulted in formation of SCN-substituted cyclohexenes 28. 24 In both cases, the reaction proceeds via formation of intermediate nitroso compounds 26 (Scheme 9). Overall, in recent years, a number of approaches for the synthesis of isoxazoline N-oxides have been developed.…”

Section: Scheme 8 Synthesis Of 2-pyrrolidones Through Recyclization Of Isoxazoline N-oxidesmentioning

confidence: 99%

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Five-Membered Hetarene N-Oxides: Recent Advances in Synthesis and Reactivity

Ферштат

Teslenko

2021

Synthesis

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Five-membered heterocyclic N-oxides attracted special attention due to their strong application potential in medicinal chemistry and advanced materials science. In this regard, novel methods for their synthesis and functionalization are constantly required. In this short review, recent state-of-the-art achievements in the chemistry of isoxazoline N-oxides, 1,2,3-triazole 1-oxides and 1,2,5-oxadiazole 2-oxides are briefly summarized. Main routes to transition-metal-catalyzed and metal-free functionalization protocols along with mechanistic considerations are outlined. Transformation patterns of the hetarene N-oxide rings as precursors to other nitrogen heterocyclic systems are also presented.

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Section: Scheme 7 Cyclization Of Gem-bromonitromethanes 19 With Alkenesmentioning

confidence: 99%

Section: Scheme 8 Synthesis Of 2-pyrrolidones Through Recyclization Of Isoxazoline N-oxidesmentioning

confidence: 99%

Five-Membered Hetarene N-Oxides: Recent Advances in Synthesis and Reactivity

Ферштат

Teslenko

2021

Synthesis

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“…Indoles were converted to corresponding thiocyanato derivatives on treatment with ammonium thiocyanate in the presence of ptoluene sulfonic acid [28]. An NBS-mediated procedure was developed for the thiocyanation of cyclohexene-fused isoxazoline N-oxides under mild conditions [29]. Several methods have been tried for the synthesis of thiocyanatoaniline.…”

Section: Introductionmentioning

confidence: 99%

An Efficient and Eco-Friendly Procedure for Electrophilic Thiocyanation of Anilines and 1-(Substituted benzylidene)-2-phenyl Hydrazines

Mallikarjunaswamy,

Kuruvalli,

Syed

et al. 2024

Chemistry

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Thiocyanates form an important class of organic compounds commonly found in natural products that exhibit excellent antimicrobial activity. The electrophilic thiocyanation is one of the most effective methods of introducing a -SCN functional group to the parent organic molecule. In this work, we explored an eco-friendly and highly efficient method for thiocyanation of anilines and 1-(substituted benzylidene)-2-phenylhydrazines using commercially available N-bromoscuccinimide (NBS) and potassium thiocyanate (KSCN). The optimized protocol afforded thiocyanates with good regioselectivity and excellent yields in comparison to the available methods.

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Rapid, Operationally Simple, and Metal‐free NBS Mediated One‐pot Synthesis of 1,2‐Naphthoquinone from 2‐Naphthol

Sim

Choi

et al. 2017

Adv Synth Catal

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A metal-free, one-pot synthesis of 1,2naphthoquinone was accomplished from 2-naphthol by utilizing economically cheap NBS under open air conditions. Initial formation of 1,1-dibromonaphthalen-2-one and subsequent transformation afforded the 1,2-naphthoquinone. This oxidation was completed within 30 min and had broad substrate scope. Moreover, this system tolerated heterocyclic systems and was also applicable to 1,3dicarbonyl systems. This practical approach with short reaction times, a simple workup, and insensitivity to moisture could override the usage of expensive and hazardous oxidizing and metal reagents.

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N‐Bromosuccinimide‐Mediated Thiocyanation of Cyclohexene‐Fused Isoxazoline N‐Oxides

Cited by 7 publications

References 62 publications

Five-Membered Hetarene N-Oxides: Recent Advances in Synthesis and Reactivity

Five-Membered Hetarene N-Oxides: Recent Advances in Synthesis and Reactivity

An Efficient and Eco-Friendly Procedure for Electrophilic Thiocyanation of Anilines and 1-(Substituted benzylidene)-2-phenyl Hydrazines

Rapid, Operationally Simple, and Metal‐free NBS Mediated One‐pot Synthesis of 1,2‐Naphthoquinone from 2‐Naphthol

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