Benzo[<i>c</i>]isothiazole 2‐Oxides: Three‐Dimensional Heterocycles with Cross‐Coupling and Functionalization Potential

Lamers, Philip; Buglioni, Laura; Koschmieder, Steffen; Chatain, Nicolas; Bolm, Carsten

doi:10.1002/adsc.201600823

Cited by 32 publications

(19 citation statements)

References 44 publications

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“…In 2016, they reported the synthesis of benzo[ c ]isothiazole 2‐oxides from 2‐( S ‐methylthiomethyl)anilines (Scheme ) . The starting material anilines were synthesized from aniline, DMSO, and TFAA via the intermediacy of S ‐dimethylsulfinimines and rearranged to the desired S ‐thiomethylated products with NaOMe.…”

Section: Synthesis Of Isothiazolesmentioning

confidence: 99%

“…Following the route described earlier, oxidative coupling between anilines and tetrahydrothiophenes in the presence of NCS and Et 3 N proceeded in 50–87% yields and was performed on a 60 mmol scale in all cases. The direct conversion to the tricyclic isothiazole derivatives was performed by reacting 2‐(tetrahydrothiophene‐2‐yl)anilines with NCS in the presence of NaOH and subsequent oxidation with m CPBA.…”

Section: Synthesis Of Isothiazolesmentioning

confidence: 99%

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Recent Advances in the Synthesis and Reactivity of Isothiazoles

2019

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Isothiazoles represent an important class of five‐membered sulfur heterocycles that are widely utilized in medicinal chemistry and organic synthesis due to the unique properties of two electronegative heteroatoms in a 1,2‐relationship. However, in contrast to other 1,2‐azoles, the facile assembly of isothiazoles has always been considered a substantial challenge. In the last decade, major advances have taken place in the fields of synthesis and functionalization of isothiazoles that make them accessible to a wide range of interested chemists through unprecedented pathways. New condensation methods have emerged that address the challenges posed by unstable thiohydroxylamine. New metal‐catalyzed approaches have been reported that deliver densely decorated isothiazoles bearing various sensitive functional groups. New functionalization strategies have been developed through both cross‐coupling and direct C−H activation chemistry. Finally, the emergence of novel heterocyclic architectures based on isothiazole opens the door for future investigations of this versatile heterocyclic scaffold. This review covers the period from January 2004 to December 2018 and is intended as a sequel to the review on isoxazoles, which represent another class of synthetically‐important 1,2‐azoles (see Adv. Synth. Catal. 2015, 357, 2583–2614).

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Section: Synthesis Of Isothiazolesmentioning

confidence: 99%

Section: Synthesis Of Isothiazolesmentioning

confidence: 99%

Recent Advances in the Synthesis and Reactivity of Isothiazoles

2019

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“…In the light of this continuous interest in the HLF reaction and based on our long‐lasting sulfur chemistry program, we wondered if appropriately substituted sulfoximine derivatives would also undergo HLF‐type cyclization reactions opening a straightforward access to synthetically interesting dihydroisothiazole oxides 2 . Considering previous reports, the iodine strategy appeared most attractive for the envisaged transformation, and S ‐phenyl‐ S ‐phenylpropyl sulfoximine ( 1 a ) was chosen as representative substrate of the initial experiments .…”

Section: Optimization Of the Reaction Conditions[a]mentioning

confidence: 99%

An Iodine‐Mediated Hofmann‐Löffler‐Freytag Reaction of Sulfoximines Leading to Dihydroisothiazole Oxides

et al. 2017

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“…1b ) 25 , 26 . The atroposelective procedure for other 1,2-azoles such as isoxazole, isothiazole, and its S-oxides has not been explored probably because it is difficult to simultaneously control the formation of heterocyclic ring and the atroposelective installation of a stereogenic axis 27 – 29 . In particular, the stereoselective construction of axially chiral isothiazole S-oxides is more difficult because an extra stereogenic sulfur center affects the synthesis of structures bearing different types of chiralities 30 , 31 .…”

Section: Introductionmentioning

confidence: 99%

Organocatalytic atroposelective construction of axially chiral N, N- and N, S-1,2-azoles through novel ring formation approach

et al. 2022

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Abstract1,2-Azoles are privileged structures in ligand/catalyst design and widely exist in many important natural products and drugs. In this report, two types of axially chiral 1,2-azoles (naphthyl-isothiazole S-oxides with a stereogenic sulfur center and atropoisomeric naphthyl pyrazoles) are synthesized via modified vinylidene ortho-quinone methide intermediates. Diverse products are acquired in satisfying yields and good to excellent enantioselectivities. The vinylidene ortho-quinone methide intermediates bearing two hetero atoms at 5-position have been demonstrated as a platform molecule for the atroposelective synthesis of axially chiral 1,2-azoles. This finding not only enrich our knowledge of vinylidene ortho-quinone methide chemistry but also provide the easy preparation method for diverse atropisomeric heterobiaryls that were inaccessible by existing methodologies. The obtained chiral naphthyl-isothiazole S-oxides and naphthyl-pyrazoles have demonstrated their potential application in further synthetic transformations and therapeutic agents.

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Benzo[c]isothiazole 2‐Oxides: Three‐Dimensional Heterocycles with Cross‐Coupling and Functionalization Potential

Cited by 32 publications

References 44 publications

Recent Advances in the Synthesis and Reactivity of Isothiazoles

Recent Advances in the Synthesis and Reactivity of Isothiazoles

An Iodine‐Mediated Hofmann‐Löffler‐Freytag Reaction of Sulfoximines Leading to Dihydroisothiazole Oxides

Organocatalytic atroposelective construction of axially chiral N, N- and N, S-1,2-azoles through novel ring formation approach

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