Three‐Dimensional Heterocycles by Iron‐Catalyzed Ring‐Closing Sulfoxide Imidation

Yu, Hao; Li, Zhen; Bolm, Carsten

doi:10.1002/anie.201804284

Cited by 49 publications

(13 citation statements)

References 93 publications

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“…The catalytic process is based on a commercially available Fe(II) phthalocyanine (FePc) as catalyst for these for ring-closing sulfur imidations and exhibits large functional group tolerance. Toluene was chosen as the solvent and the yields were higher at 100 • C [117]. Under the best conditions studied and using 5 mol% of catalyst, several 3-azidoalkyl sulfoxides underwent intramolecular imidation, giving rise to the corresponding cyclized products with yields up to 98% (Scheme 63) [117].…”

Section: Scheme 53 Aziridination Of Styrene With Arylsulfonyl Azidesmentioning

confidence: 99%

Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 1—Azides, Porphyrins and Corroles

et al. 2020

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Azides and porphyrinoids (such as porphyrin and corrole macrocycles) can give rise to new derivatives with significant biological properties and as new materials’ components. Significant synthetic approaches have been studied. A wide range of products (e.g., microporous organic networks, rotaxane and dendritic motifs, dendrimers as liquid crystals, as blood substitutes for transfusions and many others) can now be available and used for several medicinal and industrial purposes.

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Section: Scheme 53 Aziridination Of Styrene With Arylsulfonyl Azidesmentioning

confidence: 99%

Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 1—Azides, Porphyrins and Corroles

et al. 2020

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“…More recently, Bolm and co‐workers reported the synthesis of novel isothiazole derivatives by an iron‐catalyzed sulfoxide imidation (Scheme ) . Thus, azido‐substituted sulfoxides upon treatment with Fe(II)Pc (Pc=phthalocyanine) as the catalyst underwent ring‐closing sulfur imidation reactions delivering directly 4,5‐dihydro‐3 H ‐isothiazole 1‐oxides (Scheme , top ) and benzofused 3 H ‐1λ 4 ‐isothiazole 1‐oxides (Scheme , bottom ) in high to excellent yields.…”

Section: Synthesis Of Isothiazolesmentioning

confidence: 99%

“… Synthesis 4,5‐dihydro‐3 H ‐isothiazole 1‐oxides and 3 H ‐1λ 4 ‐arylo[ d ]isothiazole 1‐oxides via iron‐catalyzed sulfoxide imidation by Bolm …”

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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“…The six‐membered cyclic homologue 3 bb (see Table ) was prepared in a similar manner. Recently, Bolm and co‐workers reported an approach, with broad functional‐group tolerance, to five‐ and six‐membered cyclic sulfoximines 3 by intramolecular imidation of azido‐containing sulfoxides with a commercially available iron(II) phthalocyanine as catalyst . Moreover, Maruoka and co‐workers have outlined a procedure for the synthesis of unsaturated five‐membered cyclic sulfoximines from N ‐propargylsulfinamides through sulfur–carbon bond formation …”

Section: Introductionmentioning

confidence: 99%

Increasing Complexity: A Practical Synthetic Approach to Three‐Dimensional, Cyclic Sulfoximines and First Insights into Their in Vitro Properties

Boulard

Zibulski

Oertel

et al. 2020

Chemistry A European J

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A short synthetic approach with broad scope to access five‐ to seven‐membered cyclic sulfoximines in only two to three steps from readily available thiophenols is reported. Thus, simple building blocks were converted to complex molecular structures by a sequence of S‐alkylation and one‐pot sulfoximine formation, followed by intramolecular cyclization. Seventeen structurally diverse cyclic sulfoximines were prepared in high overall yields. In vitro evaluation of these underrepresented, three‐dimensional, cyclic sulfoximines with respect to properties relevant to medicinal chemistry did not reveal any intrinsic flaw for application in drug discovery.

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Three‐Dimensional Heterocycles by Iron‐Catalyzed Ring‐Closing Sulfoxide Imidation

Cited by 49 publications

References 93 publications

Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 1—Azides, Porphyrins and Corroles

Azides and Porphyrinoids: Synthetic Approaches and Applications. Part 1—Azides, Porphyrins and Corroles

Recent Advances in the Synthesis and Reactivity of Isothiazoles

Increasing Complexity: A Practical Synthetic Approach to Three‐Dimensional, Cyclic Sulfoximines and First Insights into Their in Vitro Properties

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