1621962-30-8 | Heterocyclic Building Blocks-Benzoxazole

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

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.

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

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

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, 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

[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

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

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

Ma, Ding’s team published research in Organic Letters in 2022-03-25 | CAS: 1621962-30-8

Introduction of Lipophilic Side-Chains to NH-Sulfoximines by Palladium Catalysis Under Blue Light Irradiation. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Palladium catalysis under blue (LED) light irradiation allows to convert NH-sulfoximines into products with long lipophilic side-chains attached to the S=N moiety. The three-component reactions involve both radicals and organometallic intermediates stemming from alkyl bromides and butadienes. The substrate scope is broad, and the products are formed in moderate to good yields.

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

Zheng, Guangfan’s team published research in Organic Chemistry Frontiers in 2018 | CAS: 1621962-30-8

Rhodium(III)-catalyzed annulative coupling between arenes and sulfoxonium ylides via C-H activation. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

An efficient strategy was developed for the synthesis of 1,2-benzothiazines and isoquinolines I [R = H, 6-Me, 8-F, etc.; R1 = Me, Ph, NHPh, etc.; R2 = Me, t-Bu, 2-FC6H4, etc.; X = C, S(O)] via Rh-catalyzed annulative coupling of aryl-imines/sulfoximines with sulfoxonium ylides. This protocol was also extended for the synthesis of isoquinoline-N-oxides such as II [R3 = Me, Et; R4 = H, 6-t-Bu, 7-Cl, etc.; Ar = Ph, 2-MeC6H4, 4-FC6H4, etc.] and naphthoimidazo[1,2-a]pyridines III [R5 = H, 2-Me, 3-Cl, etc.] from ketoximes and 2-arylimidazo[1,2-a]pyridines resp.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Teng, Fan’s team published research in Organic Letters in 2015-06-19 | CAS: 1621962-30-8

Silver-Mediated N-Trifluoromethylation of Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

An unprecedented approach to N-trifluoromethylations of electron-rich nucleophilic sites following a radical pathway is reported. Accordingly, various sulfoximines (19 examples) have been N-trifluoromethylated, providing previously unreported products with satisfying functionality tolerance in moderate to good yields. With a C-N bond length at the N-CF3 moiety of 1.341 ? the resp. linkage is shorter than a traditional C-N single bond and comparable with that of a C-N double bond.

Silver-Mediated N-Trifluoromethylation of 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