M.W=150-200 | Heterocyclic Building Blocks-Benzoxazole

Wang, Chenyang’s team published research in Organic Chemistry Frontiers in 2021 | CAS: 4381-25-3

Visible light-promoted NH-halogenation of sulfoximines with dichloromethane or dibromomethane. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

(S-Methylsulfonimidoyl)benzene (BD302898) is a building block containing a sulfoximine group. Several CDK and ATR inhibitors have exemplified the utilization of the NH sulfoximine group as abioisostere for a sulfonamide group to overcome the main project hurdles of aqueous solubility, sulfonamide-mediated off-target activity and IP. Moreover, its NH group could be expediently further functionalized through Buchwald-Hartwig coupling reaction and multifarious nucleophilic reactions.. Recommended Products is: 83730-53-4 and 1621962-30-8.

In visible light, dichloro- and dibromomethane are the halogen sources for converting NH-sulfoximines to their corresponding N-halo derivatives via an in-situ formed sulfoximidoyl-containing hypervalent iodine reagent. The reactions proceeded in air and were catalyst- and additive-free. The products were obtained in good to excellent yields.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Chenyang’s team published research in Organic Letters in 2021-09-03 | CAS: 1621962-30-8

Photocatalytic Synthesis of Difluoroacetoxy-containing Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

4-(S-Methylsulfonimidoyl)benzonitrile (BD00975057) is a building block containing a sulfoximine group. Several CDK and ATR inhibitors have exemplified the utilization of the NH sulfoximine group as abioisostere for a sulfonamide group to overcome the main project hurdles of aqueous solubility, sulfonamide-mediated off-target activity and IP. Moreover, its NH group could be expediently further functionalized through Buchwald-Hartwig coupling reaction and multifarious nucleophilic reactions.. Recommended Products is: 4381-25-3 and 83730-53-4.

[Bis(difluoroacetoxy)iodo]benzene and NH-sulfoximines reacted to give new hypervalent iodine(III) reagents, which under photocatalysis transferred difluoroacetoxy and sulfoximidoyl groups to styrenes with high regioselectivity. The results of mechanistic investigations suggested the intermediacy of radicals and revealed the importance of the difluoroacetoxy group on the iodine reagent.

Photocatalytic Synthesis of Difluoroacetoxy-containing Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wimmer, Alexander’s team published research in Advanced Synthesis & Catalysis in 2018 | CAS: 1621962-30-8

Visible-Light-Mediated Photoredox-Catalyzed N-Arylation of NH-Sulfoximines with Electron-Rich Arenes. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

The direct C-H/N-H dehydrogenative cross-coupling of NH-sulfoximines with electron-rich arenes was realized by oxidative visible-light photoredox catalysis, applying 9-mesityl-10-methylacridinium perchlorate as an organic photocatalyst. Sulfoximines display diverse desirable properties for medicinal chem. and the pharmaceutical industry. However, their preparation is still challenging. Our reaction proceeds without sacrificial oxidant, at room temperature and is highly selective for the C-N bond forming reaction. The scope of the reaction includes mono- and multi-alkylated and halogenated arenes, which are reacted with aromatic and aliphatic electron-rich and electron-poor NH-sulfoximines, giving moderate to excellent yields of the N-arylated sulfoximines. In addition, we successfully conducted the developed reaction on a gram scale (1.5 g). Mechanistic investigations show that both arene and NH-sulfoximine interact with the excited-state of the photocatalyst. We propose a radical-based mechanism, where both the arene and the NH-sulfoximine are photo-oxidized to their resp. radical intermediates. Radical-radical cross-coupling subsequently leads to the N-arylated sulfoximine. Two electrons and two protons are released during the reaction and are subsequently converted into H2 by a proton-reducing cobalt-catalyst.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Jianping’s team published research in Tetrahedron Letters in 2017-01-25 | CAS: 1621962-30-8

Eaton’s reagent-mediated metal-free and efficient synthesis of NH-sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

NH-sulfoximines were prepared efficiently from corresponding sulfoxides in the presence of sodium azide and Eaton’s reagent. This metal-free and efficient methodol. was applicable to a wide variety of functionalized sulfoxides to afford NH-sulfoximines in good to excellent yields with shorter reaction time than previously reported methods.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Goldberg, Frederick W.’s team published research in Tetrahedron in 2014-09-16 | CAS: 1621962-30-8

General synthetic strategies towards N-alkyl sulfoximine building blocks for medicinal chemistry and the use of dimethylsulfoximine as a versatile precursor. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

The sulfoximine group has great potential as a substituent in drug discovery, as evidenced by two new clin. candidates, and can be viewed as an isosteric alternative to the commonly used sulfone. Our aim was to improve the accessibility of this group by synthesizing a diverse range of S-alkyl and N-alkyl sulfoximine building blocks with procedures that are applicable on a practical scale (>10 g). In particular, synthesis of the less well exploited N-alkyl sulfoximines and the use of dimethylsulfoximine as a versatile, com. available precursor is discussed.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Zhou, Tao’s team published research in Journal of the American Chemical Society in 2021-05-12 | CAS: 4381-25-3

Efficient Synthesis of Sulfur-Stereogenic Sulfoximines via Ru(II)-Catalyzed Enantioselective C-H Functionalization Enabled by Chiral Carboxylic Acid. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

A Ru(II)-catalyzed enantioselective C-H activation/annulation of sulfoximines with ¦Á-carbonyl sulfoxonium ylides using a novel class of chiral binaphthyl monocarboxylic acids as chiral ligands, which can be easily and modularly prepared from 1,1′-binaphthyl-2,2′-dicarboxylic acid to give benzo[e][1,2]thiazine 1-oxide derivatives I [R = i-Pr, 2-furyl, Ph, etc.; Ar = Ph, 3-ClC6H4, 4-F3CC6H4, 2-FC6H4, etc.] was described. A broad range of sulfur-stereogenic sulfoximines were prepared in high yields with excellent enantioselectivities (up to 99% yield and 99% ee) via desymmetrization, kinetic resolution, and parallel kinetic resolution Furthermore, the resolution products can be easily transformed to chiral sulfoxides and key intermediates for kinase inhibitors.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Chen, Lu’s team published research in Organic & Biomolecular Chemistry in 2022 | CAS: 1621962-30-8

Rhodium(III)-catalyzed cascade C-H functionalization/annulation of sulfoximines with iodonium ylides for the synthesis of cyclohexanone-1,2-benzothiazines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

A highly efficient Rh(III)-catalyzed cascade C-H activation/annulation of sulfoximines 2-R-3-R1-4-R2C6H2S(O)(=NH)R3 (R = H, Me, OMe, Cl, Br; R1 = H, Me, OMe, Br, NO2; R2 = H, F, CN, C(O)Me, etc.; R1R2 = -CH=CH-CH=CH-; R3 = Me, Et, Bn, etc.) with iodonium ylides I (n = 0, 1; R4 = H, Me, Ph; R5 = H, Me) under metal-oxidant-free conditions has been reported. The fused cyclohexanone-1,2-benzothiazine scaffolds II is readily achieved with a one-pot process in this reaction. This protocol exhibits good functional group tolerance and moderate to excellent yields. Addnl., the olefination of the target product II (n = 1; R = R1 = R2 = H; R3 = Me; R4 = R5 = H) illustrates the promising usefulness of this strategy.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Kong, Deshen’s team published research in ACS Sustainable Chemistry & Engineering in 2022-03-07 | CAS: 4381-25-3

Mechanochemical Solvent-Free N-Sulfenylations of Sulfoximines and Sulfonimidamides. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Mechanochem. N-sulfenylations of sulfoximines and sulfonimidamides mediated by silver oxide under solvent-free conditions has been developed. The reactions are easy to perform and proceed well on a gram scale. A wide range of functional groups in the substrates were tolerated. Compared to its solvent-based counterpart, the mechanochem. approach showed significant ecol. advantages.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Huang, Gao’s team published research in Organic & Biomolecular Chemistry in 2021 | CAS: 1621962-30-8

Rhodium-catalyzed C-H activation/cyclization of aryl sulfoximines with iodonium ylides towards polycyclic 1,2-benzothiazines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

The synthesis of 1,2-benzothiazine derivatives through rhodium-catalyzed C-H activation/cyclization of S-aryl sulfoximines with iodonium ylides was developed for the first time. In this report, C-H and N-H bond functionalization was realized towards a series of tricyclic and tetracyclic sulfoximine derivatives with moderate to excellent yields under simple reaction conditions.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Zhang, Guocai’s team published research in ChemSusChem in 2020-03-01 | CAS: 1621962-30-8

Synthesis of NH-Sulfoximines by Using Recyclable Hypervalent Iodine(III) Reagents under Aqueous Micellar Conditions. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

FwThe synthesis of NH-sulfoximines I [R = Ph, Bn, 3-ClC6H4, etc.; R1 = Me, Et, Ph, etc.] from sulfides was developed under mild conditions in an aqueous solution with surfactant TPGS-750-M as catalyst and recyclable hypervalent iodine(III) reagent at room temperature A newly developed hypervalent iodine(III) reagent could readily oxidize sulfides and afforded the corresponding trifluoroiodobenzene, which could be efficiently recovered from the reaction mixture by a simple liquid-liquid biphasic extraction procedure. This protocol was compatible with a broad range of functional groups and could be easily performed on a gram scale, providing a green protocol for the synthesis of compounds I.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem