1621962-30-8 | Page 2 of 3 | Heterocyclic Building Blocks-Benzoxazole

Zhu, Hui’s team published research in Tetrahedron Letters in 2016-06-01 | CAS: 1621962-30-8

Radical N-arylation/alkylation of 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.

A novel copper-catalyzed N-arylation/alkylation of acyl peroxides RC(O)O2C(O)R [R = CH3(CH2)8, 4-H3CC6H4, 4-FC6H4, 3-ClC6H4, etc.] with sulfoximines R1R2S(O)(=NH) (R1 = C6H5, 2-ClC6H4, biphenyl-4-yl, etc.; R2 = CH3, 4-H3CO2CC6H4, 4-BrC6H4, etc.) as aryl/alkyl source was developed. This approach undergoes a radical pathway, representing an alternative complement to construct N-arylated/alkylated sulfoximines R1R2S(O)(=NR).

Radical N-arylation/alkylation 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

Wimmer, Alexander’s team published research in Organic Letters in 2019-04-19 | CAS: 1621962-30-8

N-Arylation of NH-Sulfoximines via Dual Nickel Photocatalysis. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

The pharmaceutically underexplored sulfoximine moiety has emerged as a potentially active pharmaceutical ingredient. We developed a scalable synthetic route to N-arylated sulfoximines from the resp. “”free”” NH-sulfoximines and bromoarenes. Our strategy is based on a dual nickel photocatalytic approach, is applicable for a broad scope of substrates, and exhibits a highly functional group tolerance. In addition, we could demonstrate that other sulfoximidoyl derivatives like sulfonimidamides and sulfinamides proceed smoothly under the developed reaction conditions.

N-Arylation of NH-Sulfoximines via Dual Nickel Photocatalysis. 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

Guo, Sheng-rong’s team published research in Tetrahedron Letters in 2017-07-05 | CAS: 1621962-30-8

Palladium catalyzed aroylation of NH-sulfoximines with aryl halides using chloroform as the CO precursor. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

A palladium-catalyzed aroylation of NH-sulfoximines for the efficient synthesis of N-aroyl sulfoximines from aryl halides and chloroform was developed. The mild reaction conditions (temperature, catalyst loading) and the use of a CO surrogate rendered this transformation a useful method for the synthesis of N-aroyl sulfoximines from available feedstock.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Tu, Yongliang’s team published research in Organic Letters in 2022-01-28 | CAS: 1621962-30-8

Visible-Light-Mediated ¦Á-Ketoacylations of NH-Sulfoximines with gem-Difluoroalkenes. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

A photochem. approach for the preparation of ¦Á-keto-N-acyl sulfoximines ArC(O)C(O)N=S(R)(R1)=O (Ar = 2-naphthyl, 3-chlorophenyl, 4-bromophenyl, etc.; R = Me, Et, t-Bu, Bn; R1 = Me, Ph, 2-chlorophenyl, etc.) from NH sulfoximines NH=S(R)(R1)=O and gem-difluoroalkenes ArCH=CF2 has been developed. In the presence of NBS, the reactions proceed in air without the need of a photocatalyst or addnl. oxidant. Results of mechanistic studies suggest that the two oxygens in the products stem from water and dioxygen.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Chenyang’s team published research in Organic Letters in 2020-11-20 | CAS: 1621962-30-8

Use of Hypervalent Iodine Reagents in Visible Light-Promoted ¦Á-Ketoacylations of Sulfoximines with Aryl Alkynes. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

In visible light, sulfoximidoyl-containing hypervalent iodine reagents react with aryl alkynes to give N-¦Á-ketoacylated sulfoximines in good to high yields. The process is metal- and base-free, providing the diketonic products without the use of highly oxygenated reagents such as peroxides. Results from mechanistic investigations suggest the intermediacy of radicals and reveal the importance of mol. oxygen.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Xu, Jian’s team published research in Organic Chemistry Frontiers in 2017 | CAS: 1621962-30-8

Synthesis of fully-substituted 1,2,3-triazoles via copper(I)-catalyzed three-component coupling of sulfoximines, alkynes and azides. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

A copper(I)-catalyzed three-component reaction of alkynes RCCH (R = C6H5, biphenyl-4-yl, naphthalen-1-yl, etc.), sulfoximines R1(R2)S(=NH)(O) [R1R2 = -(CH2)4-; R1 = C6H5, 4-FC6H4, 4-ClC6H4, 4-NCC6H4; R2 = CH3, CH2CH3] and azides R3N3 [R3 = 4-BrC6H4CH2, cyclohexyl, 2-(naphthalen-1-yl)ethyl, etc.] is described. This reaction proceeds under mild conditions with copper salt as a catalyst and atm. oxygen as an oxidant to afford a variety of 1,2,3-triazolyl-5-sulfoximines I in moderate to good yields.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Kong, Xianqiang’s team published research in Journal of Organic Chemistry in 2021-10-01 | CAS: 1621962-30-8

Electrochemical Oxidative C(sp3)-H/N-H Coupling of Diarylmethanes with Sulfoximines or Benzophenone Imine. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

An efficient electrochem. method for the synthesis of N-alkylated sulfoximines I [R = Ph, 2-BrC6H4, 4-MeOC6H4, etc.; R1 = Me, Et, n-Bu, Ph, 4-MeC6H4; Ar1 = Ph, 4-FC6H4, 4-ClC6H4; Ar2 = Ph, 4-FC6H4] by electrochem. oxidative C(sp3)-H/N-H coupling of sulfoximines and diarylmethanes was developed. In addition, used the same conditions for electrochem. dehydrogenative amination of diarylmethanes with benzophenone imine as an aminating agent to obtain II [Ar3 = Ph, 4-MeC6H4, 4-FC6H4; Ar4 = Ph, 4-MeC6H4, 4-FC6H4, 4-ClC6H4]. The reactions showed good functional group tolerance and afforded the corresponding products in moderate to good yields without the use of a stoichiometric oxidant, a metal catalyst, or an activating agent.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Chenyang’s team published research in Angewandte Chemie, International Edition in 2020-08-03 | CAS: 1621962-30-8

Photocatalytic Fluoro Sulfoximidations of Styrenes. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Reactions of difluoroiodotoluene with NH-sulfoximines provide new hypervalent iodine(III) reagents, which photocatalytically transfer a fluoro and a sulfoximidoyl group onto styrenes with high regioselectivity [e.g., stepwise I + II followed by treatment with styrene and photocatalyst under blue LED ¡ú III (83%, diastereomer mix)]. The substrate scope is broad with respect to both sulfoximines and olefins. Following an operationally simple protocol, a large library of fluorine-containing N-functionalized sulfoximines can be accessed. Results from mechanistic investigations revealed the importance of radical intermediates.

Photocatalytic Fluoro Sulfoximidations of Styrenes. 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

Aher, Yogesh N.’s team published research in Chemical Communications (Cambridge, United Kingdom) in 2018 | CAS: 1621962-30-8

Cp*Ir(III)-catalyzed C-H/N-H functionalization of sulfoximines for the synthesis of 1,2-benzothiazines at room temperature. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

The first Cp*Ir(III)-catalyzed C-H/N-H bond functionalization of sulfoximines with ¦Á-diazocarbonyl compounds has been developed for the synthesis of 1,2-benzothiazines under redox-neutral conditions. The reactions proceed at room temperature with excellent functional group tolerance and high yields without the requirement of any silver additive.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Shi, Peng’s team published research in Organic Letters in 2020-11-20 | CAS: 1621962-30-8

Synthesis of Benzothiadiazine-1-oxides by Rhodium-Catalyzed C-H Amidation/Cyclization. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

A rhodium-catalyzed C-H amidation/cyclization sequence provides benzothiadiazine-1-oxides from sulfoximines and 1,4,2-dioxazol-5-ones in good yields. The reaction is characterized by a high functional group tolerance and, in contrast to most previous transformations of this type, is well-suited for S-alkyl-S-aryl-substituted sulfoximines.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem