50578-18-2 | Page 4 of 5 | Heterocyclic Building Blocks-Benzoxazole

Yoshida, Suguru’s team published research in Chemistry Letters in 2017-01-31 | CAS: 50578-18-2

Reactions of arynes with sulfoximines: formal sulfinylamination vs. N-arylation. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

1-Iminotetrahydrothiophene 1-oxide (BD00963737) 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.

Reactions of arynes with sulfoximines were reported. The fate of these reactions depended on the substituents of the sulfoximines. S,S-Diarylsulfoximines reacted with arynes to selectively afford o-sulfinylanilines, whereas a simple N-arylation reaction was observed when S-alkyl-S-aryl- or S,S-dialkylsulfoximine was used to selectively afford the corresponding N-arylated sulfoximines.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Aithagani, Sravan Kumar’s team published research in Journal of Organic Chemistry in 2016-07-15 | CAS: 50578-18-2

Metal-Free, Phosphonium Salt-Mediated Sulfoximination of Azine N-Oxides: Approach for the Synthesis of N-Azine Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

Herein, we report a simple and metal-free method for the synthesis of N-azine sulfoximines by the nucleophilic substitution of azine N-oxides with NH-sulfoximines. The present method works at room temperature with wide functional group compatibility and gives several unprecedented N-azine sulfoximines. The reaction conditions were also found suitable with enantiopure substrates and furnished products without any racemization. It also finds an application in the sulfoximination of azine-based functional mols. such as 2,2′-bipyridine, 1,10-phenanthroline, and quinine.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Furukawa, Naomichi’s team published research in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1981-03-31 | CAS: 50578-18-2

Enhanced reactivities in substitution and elimination reactions in dimethyl sulfoximide. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

The preparation and dielec. constants of di-Me sulfoximide (I), tetramethylene sulfoximide, and di-Me N-methylsulfoximide are reported, and the kinetics examined for typical nucleophilic substitution and base-catalyzed elimination reactions in I as solvent. The rate enhancements indicate that the sulfoximides belong to a new type of solvent which is protic but behaves like a characteristic polar aprotic solvent. Also reported is the solvolysis of alkyl toluenesulfonates and halides in I to give the corresponding N-alkyl sulfoximides. Thus, octyl toluenesulfonate was heated in I at 95¡ã for 20 h to give 83% di-Me N-octylsulfoximide.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Zenzola, Marina’s team published research in Angewandte Chemie, International Edition in 2016 | CAS: 50578-18-2

Transfer of Electrophilic NH Using Convenient Sources of Ammonia: Direct Synthesis of NH Sulfoximines from Sulfoxides. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

A new system for NH transfer is developed for the preparation of sulfoximines, which are emerging as valuable motifs for drug discovery. The protocol employs readily available sources of nitrogen without the requirement for either preactivation or for metal catalysts. Mixing ammonium salts with diacetoxyiodobenzene directly converts sulfoxides into sulfoximines. This report describes the first example of using of ammonia sources with diacetoxyiodobenzene to generate an electrophilic nitrogen center. Control and mechanistic studies suggest a short-lived electrophilic intermediate, which is likely to be PhINH or PhIN+.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Yu, Hao’s team published research in Angewandte Chemie, International Edition in 2018-01-01 | CAS: 50578-18-2

Iron(II)-Catalyzed Direct Synthesis of NH Sulfoximines from Sulfoxides. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

Free NH-sulfoximines were directly prepared from sulfoxides through iron catalysis by applying a readily available, shelf-stable hydroxylamine triflic acid salt. No addnl. oxidant is needed, and the substrate scope is broad, including a range of heterocyclic compounds Thus, e.g., imidation of PhS(:O)Me with O-(4-nitrobenzoyl)hydroxylamine.HOTF in presence of FeSO4 and 1,10-phenanthroline afforded PhS(:O)(:NH)Me (98%, 93% isolated).

Iron(II)-Catalyzed Direct Synthesis of NH Sulfoximines from Sulfoxides. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Luan, Nannan’s team published research in Tetrahedron Letters in 2020-01-02 | CAS: 50578-18-2

PhI(OAc)2-mediated oxidative C-H sulfoximination of imidazopyridines under mild conditions. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

A facile protocol for direct oxidative C-N bond coupling of unactivated imidazo[1,2-a]pyridines with NH-sulfoximines was disclosed using sulfoximines as the nitrogen sources in the presence of (diacetoxy)iodobenzene (PhI(OAc)2). The reaction proceeded smoothly under air without any metal catalyst to give a series of C-3 sulfoximidoyl-functionalized imidazo[1,2-a]pyridines products regioselectively.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Zou, Ya’s team published research in Chemical Communications (Cambridge, United Kingdom) in 2015 | CAS: 50578-18-2

Transition metal-free aroylation of NH-sulfoximines with methyl arenes. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

A novel protocol towards N-aroylated sulfoximines from NH-sulfoximines and Me arenes is demonstrated. The reaction took place in the presence of elemental iodine, requiring no external organic solvents, transition metal-catalysts or ligands. The aroylated products were obtained from the oxidative transformation in moderate to excellent yields (up to 94% yield) with a broad substrate scope through a radical pathway.

Transition metal-free aroylation of NH-sulfoximines with methyl arenes. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Garcia Mancheno, Olga’s team published research in Organic Letters in 2007-09-13 | CAS: 50578-18-2

Iodinane- and Metal-Free Synthesis of N-Cyano Sulfilimines: Novel and Easy Access of NH-Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

The synthesis of N-cyanosulfilimines can readily be achieved by reaction of the corresponding sulfides with cyanogen amine in the presence of a base and NBS or I2 as halogenating agents. E.g., imination of PhSMe by H2NCN/NBS/t-BuOK gave 91% PhSMe:NCN. Oxidation followed by C-N bond cleavage affords synthetically useful NH-free sulfoximines, e.g., I.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Lin, Yan’s team published research in ACS Sustainable Chemistry & Engineering in 2018-11-05 | CAS: 50578-18-2

Green and Efficient Synthesis of N-Sulfenyl Sulfoximines in Water. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

A new and metal-free cross-coupling reaction between sulfoximines and N-(phenylthio)succinimides was developed in water, affording an efficient route for the synthesis of N-sulfenyl sulfoximines. This transformation provides N-sulfenyl sulfoximines with good functional group tolerance and moderate to excellent yields. Moreover, this protocol can be easily scaled up to the gram level with excellent yield.

Green and Efficient Synthesis of N-Sulfenyl Sulfoximines in Water. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Siu, Tung’s team published research in Organic Letters in 2002-05-30 | CAS: 50578-18-2

Electrochemical Imination of Sulfoxides Using N-Aminophthalimide. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

A novel electrochem. sulfoxide imination process is described. Our approach starts with a highly selective nitrene transfer from N-aminophthalimide to a variety of sulfoxides. This oxidative treatment is followed by reductive N-N bond cleavage under the controlled current conditions, which leads to a range of parent NH sulfoximines. In addition to solving the challenging problem of removing the N-phthalimido group, the overall process avoids the use of toxic oxidants and metal additives.

Electrochemical Imination of Sulfoxides Using N-Aminophthalimide. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem