4381-25-3 | Page 3 of 5 | Heterocyclic Building Blocks-Benzoxazole

Wang, Chenyang’s team published research in Organic Letters in 2020-11-20 | CAS: 4381-25-3

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

(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, 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

Huang, Gao’s team published research in Organic & Biomolecular Chemistry in 2021 | CAS: 4381-25-3

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

Shi, Peng’s team published research in Organic Letters in 2020-11-20 | CAS: 4381-25-3

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

Chen, Hongyi’s team published research in Green Chemistry in 2021 | CAS: 4381-25-3

Blue light-promoted radical sulfoximido-chalcogenization of aliphatic and aromatic alkenes. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

A transition metal-free synthesis of N-(arylthio/seleno)ethyl sulfoxidmines via blue light-promoted radical sulfoximido-chalcogenization of aliphatic and aromatic alkenes was developed. The sulfoximidation process demonstrated high chemoselectivity and allowed a broad substrate scope, completing the sulfoximido-chalcogenization of alkenes in good yields.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Zhang, Guocai’s team published research in ChemSusChem in 2020-03-01 | CAS: 4381-25-3

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

Grandhi, Gowri Sankar’s team published research in Organic Letters in 2020-04-03 | CAS: 4381-25-3

Copper-Catalyzed 8-Aminoquinoline-Directed Oxidative C-H/N-H Coupling for N-Arylation of Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

A copper-catalyzed cross-dehydrogenative C-H/N-H coupling has been devised to access a series of N-arylated sulfoximines, e,g., I, in high yield from 8-aminoquinoline-derived benzamides and sulfoximines. The reaction is scalable, and mechanistic studies favor the involvement of an organometallic pathway, where C-H bond cleavage is presumed to be the kinetically relevant step. The utility of sulfoximine-coupled benzamides was displayed through the nickel-catalyzed acceptorless dehydrogenative olefination of benzyl alcs.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Rajbongshi, Kamal K.’s team published research in Synthesis in 2020-04-30 | CAS: 4381-25-3

Microwave-Accelerated N-Acylation of Sulfoximines with Aldehydes under Catalyst-Free Conditions. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

An efficient catalyst-free radical cross-coupling reaction between sulfoximines R1S(O)(=NH)R2 [R1 = Me, Ph, 4-methoxyphenyl, 4-bromophenyl; R2 = Me, Ph; R1R2 = -(CH2)4-] and aromatic aldehydes R3CHO (R3 = 2-chlorophenyl, naphthalen-1-yl, furan-2-yl, etc.) was developed. The reaction took place in the presence of N-bromosuccinimide as the radical initiator under microwave irradiation to afford the corresponding acylated sulfoximines R1S(O)(R2)=NC(O)R3 in moderate to excellent yields (27 examples). This protocol is proved to be rapid, easy to handle, and applicable to a broad scope of substrates.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Ma, Ding’s team published research in Organic Letters in 2022-03-25 | CAS: 4381-25-3

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

Wang, Jian’s team published research in Chemistry Letters in 2022 | CAS: 4381-25-3

TEMPO/PhI(OAc)2-mediated Direct Sulfoximination of Benzoxazoles under Metal-free Conditions. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

A metal-free reaction system consisting of TEMPO and PhI(OAc)2 for the oxidative C-N coupling of benzoxazoles with NH-sulfoximines had been developed to obtain arylsulfoximines I [R1 = H, 5-Cl, 7-Br, etc.; R2 = Me, Et, n-Bu, Bn; R3 = Ph, 4-FC6H4, 2-BrC6H4, etc.]. The reaction could proceed under ambient atm. without any metal catalyst at room temperature to afford the corresponding 2-iminoazoles in moderate to high yields.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Tu, Yongliang’s team published research in Organic & Biomolecular Chemistry in 2021 | CAS: 4381-25-3

Visible light-induced C-C bond cleavage in a multicomponent reaction cascade allowing acylations of sulfoximines with ketones. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Visible light induces C-C-bond cleavage reactions of ketones, which can be utilized for N-acylations of sulfoximines. No (photo)catalyst is required, and the reactions occur at ambient temperature in air. The substrate scope is broad for both ketones and sulfoximines. For converting NH-sulfoximines, the presence of NBS is essential.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem