4381-25-3 | 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

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

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

Li, Shan’s team published research in Organic Letters in 2020-10-02 | CAS: 4381-25-3

Palladium-Catalyzed Oxidative Annulation of Sulfoximines and Arynes by C-H Functionalization as an Approach to Dibenzothiazines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

This work reports a novel and efficient palladium-catalyzed synthesis of tricyclic dibenzothiazines using easily prepared aryl sulfoximines and aryne precursors via C-H functionalization and cyclization. A mechanistic investigation indicated that the C-H bond cleavage at the position ortho to the sulfoximine group is the rate-determining step.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Hommelsheim, Rene’s team published research in Organic Letters in 2021-05-07 | CAS: 4381-25-3

2-Sulfoximidoyl Acetic Acids from Multicomponent Petasis Reactions and Their Use as Building Blocks in Syntheses of Sulfoximine Benzodiazepine Analogues. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Upon application of a multicomponent Petasis reaction, a broad range of NH-sulfoximines R1R2S(O)=NH (R1 = Ph, naphthalen-2-yl; R2 = Me, Ph, cyclopentyl, etc.) and boronic acids R3C6H5B(OH)2 (R3 = H, 4-Me, 3-SMe, 4-F, etc.) react with glyoxalic acid to afford the corresponding 2-substituted acetic acids with N-bound sulfoximidoyl groups R1R2S(O)=NCH2(R3)C(O)O(R4) (R4 = H, Me). The protocol features excellent yields under ambient, metal-free conditions and short reaction times. Furthermore, the applicability of 2-sulfoximidoyl acetic acids as building blocks for synthesizing sulfoximine-based benzodiazepine analogs (1R,3R)/(1S,3R)-I was demonstrated.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Peng, Ruyi’s team published research in Indian Journal of Heterocyclic Chemistry in 2021-09-30 | CAS: 4381-25-3

Palladium-catalyzed denitrogenative arylation of sulfoximines and sulfonamides with arylhydrazines under mild conditions. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

A Pd(II)-catalyzed direct arylation of NH-sulfoximines and sulfonamides with arylhydrazine hydrochlorides was herein demonstrated without participation of any organic ligands under mild conditions. The oxidative methodol. afforded a smooth routine toward N-aryl sulfoximines and sulfonamides with high efficiency (up to 93% yields) and broad functional groups tolerance (up to 40 examples) through a denitrogenative pathway. The protocol was proposed to take place through the free radical pathway based on the results of control reactions and literature explorations.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Baranwal, Siddharth’s team published research in Asian Journal of Organic Chemistry in 2021-07-31 | CAS: 4381-25-3

Selenium Dioxide Promoted ¦Á-Keto N-Acylation of Sulfoximines Under Mild Reaction Conditions. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

A practical method for the synthesis of ¦Á-ketoamides of sulfoximines I [R1 = Ph, 4-MeC6H4, Bn, etc.; R2 = Me, Et, Ph, etc.; R3 = H, 4-F, 2-Cl, etc.] was developed from NH-sulfoximines and acetophenones using selenium dioxide as an oxidant. The reactions proceeded under mild conditions in the absence of any additives and provided good to excellent yields of ¦Á-keto-N-acylsulfoximines. Moreover, the optimized condition was well-suited to the task of ¦Á-ketoacylation of sulfoximines with phenylacetaldehyde and arylacetylenes. ¦Á-Hydroxy N-acylsulfoximines were obtained in good yields from ¦Á-keto N-acylsulfoximines via reduction or Grignard reactions.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Li, Jun-Yi’s team published research in ACS Catalysis in 2022-08-05 | CAS: 4381-25-3

Ir(III)-Catalyzed Asymmetric C-H Activation/Annulation of Sulfoximines Assisted by the Hydrogen-Bonding Interaction. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Herein, an Ir(III)-catalyzed asym. C-H activation enabled by noncovalent interactions was described. A broad range of sulfur-stereogenic sulfoximines, e.g., I was prepared in high yields with excellent enantioselectivities via the asym. C-H activation/annulation of sulfoximines with diazo compounds Desymmetrization, kinetic resolution, and parallel kinetic resolution were compatible with this protocol. Detailed DFT calculations suggested that the N-H¡¤¡¤¡¤O hydrogen bonding interaction between sulfoximine and the chiral carboxylic acid ligand was crucial for the high enantiocontrol. Moreover, chiral iridacycle intermediates were isolated, characterized, and subjected to stoichiometric reactions. Computational and exptl. studies suggested that the C-H cleavage step was the rate- and enantio-determining step.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Feng, Tao’s team published research in Synthetic Communications in 2021 | CAS: 4381-25-3

Photocatalytic N-benzylation of NH-sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

N-Benzylation of NH-sulfoximines via visible light photocatalysis is realized. Under mild reaction conditions, photocatalyst promotes the direct cross-coupling of NH-sulfoximines with benzyl bromides to form N-benzyl sulfoximines. Superbases which are usually used in reported coupling of NH-sulfoximines with alkyl halides were not needed. This method is also suitable for the synthesis of N-allyl sulfoximines.

Photocatalytic N-benzylation of NH-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

Terhorst, Steven’s team published research in Organic Letters in 2022-06-17 | CAS: 4381-25-3

Sulfonimidamides by Sequential Mechanochemical Chlorinations and Aminations of Sulfinamides. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Here, the first mechanochem. synthesis of sulfonimidamides, e.g., I was reported. The one-pot, two-step method requires neither a solvent nor inert conditions. In a mixer mill, sulfinamides ArS(O)NH(R) (Ar = Ph, 4-methylphenyl; R = pivaloyl, Boc) are rapidly converted to sulfonimidoyl chlorides ArS(O)NR(Cl) by oxidative chlorination with N-chlorosuccinimide (NCS). Subsequent substitutions with amines such as benzyl amine, 3-methyl-1H-pyrazole, piperazine, etc. provides a wide range of diversely substituted sulfonimidamides.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem