Synthesis of 1,3-dibromo-2-aryl-1H-indenes via NBS mediated unusual bromination of 2-alkynylbenzaldoximes

Singha, Raju; Ghosh, Munmun; Das, Saikat; Das, Dhiraj; Ray, Jayanta K.

doi:10.1039/c6nj01201a

Cited by 7 publications

(5 citation statements)

References 43 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Interestingly, NCS and NIS did not afford these abnormal products. 39 Although the yields were quite low, this unusual reaction proved to be a very convenient route for the preparation of rare 2-aryl-1,3-dibromoindenes 44. Mechanistic studies indicate an initial formation of the unsaturated bromonium ion 45 that can be attacked by the nitrogen or the C=C bond, which results in the isoquinoline or indene motifs, respectively.…”

Section: Scheme 6 Synthesis Of Dihydrofuropyridinones and Furan-3(2h)mentioning

confidence: 98%

“…Mechanistic studies indicate an initial formation of the unsaturated bromonium ion 45 that can be attacked by the nitrogen or the C=C bond, which results in the isoquinoline or indene motifs, respectively. 39 Scheme 10 NXS-promoted electrophilic cyclization of 2-alk-1-ynylbenzaldoximes. Reagents and conditions: (i) NXS (1.2 equiv), CH 2 Cl 2 , rt, 20 min to 24 h; (ii) NBS (3 equiv), CH 2 Cl 2 , rt, 30 min.…”

Section: Scheme 6 Synthesis Of Dihydrofuropyridinones and Furan-3(2h)mentioning

confidence: 99%

See 1 more Smart Citation

N-Halo Reagents: Modern Synthetic Approaches for Heterocyclic Synthesis

Andrade¹,

Mattos

2019

Synthesis

View full text Add to dashboard Cite

Heterocyclic chemistry is an essential frontier in science and a source of novel biologically active compounds. The development of innovative synthetic methodologies that allows access to different heterocyclic rings is of critical interest to the scientific community. This review will focus on recent applications of N-halo compounds (e.g., N-halosuccinimides, trihaloisocyanuric acids, N-halosulfonamides, etc.) in heterocyclic construction via electrophilic cyclization, asymmetric halocyclization, oxidative cyclization, and radical processes.1 Introduction2 N-Halo Reagent Mediated Heterocyclic Construction and Functionalization2.1 Electrophilic Halocyclizations2.1.1 Asymmetric Halocyclizations2.2 Radical Halocyclizations2.3 Oxidative Halocyclizations2.4 Miscellaneous Halocyclization Reactions3 Summary and Outlook

show abstract

Section: Scheme 6 Synthesis Of Dihydrofuropyridinones and Furan-3(2h)mentioning

confidence: 98%

Section: Scheme 6 Synthesis Of Dihydrofuropyridinones and Furan-3(2h)mentioning

confidence: 99%

N-Halo Reagents: Modern Synthetic Approaches for Heterocyclic Synthesis

Andrade¹,

Mattos

2019

Synthesis

View full text Add to dashboard Cite

show abstract

“…In 2016, the Ray group re-investigated this study. As a result, it was revealed that the use of an excess of NBS leads to the formation of unusual products, 1,3-dibromo-2-aryl-1 H -indenes 54′ , in moderate to low yield [ 74 ]. The use of N -chlorosuccinimide (NCS) and NIS did not lead to these unusual products.…”

Section: Reagent-switchable Cyclizationsmentioning

confidence: 99%

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

et al. 2020

View full text Add to dashboard Cite

In organic synthesis, due to their high electrophilicity and leaving group properties, halogens play pivotal roles in the activation and structural derivations of organic compounds. Recently, cyclizations induced by halogen groups that allow the production of diverse targets and the structural reorganization of organic molecules have attracted significant attention from synthetic chemists. Electrophilic halogen atoms activate unsaturated and saturated hydrocarbon moieties by generating halonium intermediates, followed by the attack of carbon-containing, nitrogen-containing, oxygen-containing, and sulfur-containing nucleophiles to give highly functionalized carbocycles and heterocycles. New transformations of halogenated organic molecules that can control the formation and stereoselectivity of the products, according to the difference in the size and number of halogen atoms, have recently been discovered. These unique cyclizations may possibly be used as efficient synthetic strategies with future advances. In this review, innovative reactions controlled by halogen groups are discussed as a new concept in the field of organic synthesis.

show abstract

“…In 2016, the Ray group re-investigated this study. As a result, it was revealed that the use of an excess of NBS leads to the formation of unusual products, 1,3-dibromo-2-aryl-1H-indenes 54', in moderate to low yield [75]. Interestingly, the use of N-chlorosuccinimide (NCS) and NIS did not lead to these unusual products being produced.…”

Section: Other Miscellaneous Reactionsmentioning

confidence: 99%

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

China

Kumar

Kikushima

et al. 2020

Preprint

View full text Add to dashboard Cite

In organic synthesis, due to their high electrophilicity and leaving group properties, halogens play pivotal roles in the activation and structural derivations of organic compounds. Recently, cyclizations induced by halogen groups that allow the production of diverse targets and the structural reorganization of organic molecules have attracted significant attention from synthetic chemists. Electrophilic halogen atoms activate unsaturated and saturated hydrocarbon moieties via the generation of halonium intermediates, followed by the attack of carbon-, nitrogen-, oxygen-, and sulfur-containing nucleophiles to give highly functionalized carbo- and heterocycles. Interestingly, new transformations of halogenated organic molecules that can control the formation and stereoselectivity of the products according to the difference in the size and number of halogen atoms have recently been discovered. These unique cyclizations may possibly be used as efficient synthetic strategies with future advances. In this review, innovative reactions controlled by halogen groups are discussed as a new concept in the field of organic synthesis.

show abstract

Synthesis of 1,3-dibromo-2-aryl-1H-indenes via NBS mediated unusual bromination of 2-alkynylbenzaldoximes

Abstract: An interesting side-pathway leading to 1,3-dibromo-2-aryl-1H-indenes as opposed to isoquinoline N-oxides via NBS mediated bromination of 2-alkynylbenzaldoximes.

Cited by 7 publications

References 43 publications

N-Halo Reagents: Modern Synthetic Approaches for Heterocyclic Synthesis

N-Halo Reagents: Modern Synthetic Approaches for Heterocyclic Synthesis

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy

Contact Info

Product

Resources

About