145026-07-9 | Page 6 of 10 | Heterocyclic Building Blocks-Benzoxazole

Cho, Gae Young’s team published research in Organic Letters in 2004-09-16 | CAS: 145026-07-9

Copper-Mediated Cross-Coupling Reactions of N-Unsubstituted Sulfoximines and Aryl Halides. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

1-Bromo-4-(S-methylsulfonimidoyl)benzene (BD336512) 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.

Copper-mediated cross-coupling reactions of sulfoximines with aryl iodides and aryl bromides provide N-arylated sulfoximines in high yields. The method is complementary to the known palladium-catalyzed N-arylation and allows the preparation of N-arylated sulfoximines, which have previously been inaccessible.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Dong, Wanrong’s team published research in Chemistry – A European Journal in 2014 | CAS: 145026-07-9

Hydroarylations of Heterobicyclic Alkenes through Rhodium-Catalyzed Directed C-H Functionalizations of S-Aryl Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

Rhodium-catalyzed directed CH-functionalizations have been used in hydroarylations of heterobicyclic alkenes with NH-sulfoximines. Unexpectedly, the bicyclic framework is retained, resulting in the formation of addition products being attractive intermediates for functionalized mols. that are difficult to prepare by other means.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Han, Sang Hoon’s team published research in Asian Journal of Organic Chemistry in 2021-09-30 | CAS: 145026-07-9

Palladium(II)-Catalyzed N-Carbonylative Cross-Coupling Reaction of Sulfoximines with Aryl, Heteroaryl, and Alkenyl Halides Using Tungsten Hexacarbonyl as Carbon Monoxide Source. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

Palladium(II)-catalyzed N-acylation was demonstrated through the reaction of N-H sulfoximines with a variety of aryl, heteroaryl, and aryl halides using W(CO)6 as a source of carbon monoxide, affording N-acylated sulfoximines in good to excellent yields. Moreover, alkenyl bromides underwent palladium(II)-catalyzed N-acylation reactions with N-H sulfoximines, leading to the formation of N-cinnamoyl sulfoximines. This method was the advantages of a broad substrate scope, high functional group tolerance, simple operation, and chemoselectivity between chloride and bromide.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Li, Jian’s team published research in Journal of Organic Chemistry in 2021-11-05 | CAS: 145026-07-9

Sulfoximines Assisted Rh(III)-Catalyzed C-H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A facile access to highly fused tetracyclic indeno-1,2-benzothiazines has been established via a Rh(III)-catalyzed C-H bond activation and intramol. annulation cascade between sulfoximides and all-carbon diazo indandiones. This strategy is characterized by the fact that the diazo coupling partners do not require preactivation, along with its high efficiency, broad substrate generality, and facile transformation. Particularly, the highly conjugated tetracyclic products demonstrate good optical properties and can easily enter cells to emit bright fluorescence for live cell imaging.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Bohmann, Rebekka Anna’s team published research in Chemistry – A European Journal in 2016 | CAS: 145026-07-9

1,2-Thiazines: One-Pot Syntheses Utilizing Mono and Diaza Analogs of Sulfones. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A one-pot Michael addition/cyclization/condensation reaction sequence for the regioselective synthesis of 1,2-thiazines I (R1 = C6H5, 4-BrC6H4, CH3, 4-H3COC6 H4; R2 = C6H5, 4-H3CC6H4, 3-H3CC6H4, 4-F3CC6H4, 2,5-(CH3)2C6H3; R3 = 4-H3COC6H4, C(CH3)3, thiophen-2-yl, 2-naphthyl, etc.; Y = O, C6H5NH2, N(CN), 4-H3COC6H4N), starting from propargyl ketones R2CCC(O)R3 and NH-sulfoximines or NH-sulfondiimines R1S(Y)(:NH)CH3, has been developed. Under mild and operationally simple reaction conditions previously unprecedented 1,2-thiazine 1-imide and 1-oxide derivatives I are formed in good to excellent yields. The products I represent heterocyclic building blocks, readily modifiable by a regioselective C-H bond functionalization, classical cross-coupling reactions, and deprotection.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Aithagani, Sravan Kumar’s team published research in Organic Letters in 2015-11-20 | CAS: 145026-07-9

Metal-Free Approach for the Synthesis of N-Aryl Sulfoximines via Aryne Intermediate. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

A metal-free and operationally simple N-arylation of NH-sulfoximines with aryne precursors is reported. E.g., in presence of KF/18-crown-6 in THF, reaction of o-TMSC6H4OTf and PhSMe(:O):NH gave 72% PhSMe(:O):NPh. Transition metal-free reaction conditions and shorter reaction times are the highlights of the present method. The mild optimized condition was also suitable with enantiopure substrates.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Chenyang’s team published research in Organic Letters in 2020-11-20 | CAS: 145026-07-9

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/1621962-30-8.html, 50578-18-2

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

Aithagani, Sravan Kumar’s team published research in Journal of Organic Chemistry in 2016-07-15 | CAS: 145026-07-9

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, 50578-18-2

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

Miyasaka, Mitsuru’s team published research in Organic Letters in 2011-02-04 | CAS: 145026-07-9

Copper-Catalyzed Direct Sulfoximination of Azoles and Polyfluoroarenes under Ambient Conditions. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

The direct dehydrogenative C-N coupling of azoles or polyfluoroarenes with N-H sulfoximines proceeds effectively in the presence of a copper catalyst at room temperature under air to afford the corresponding N-arylsulfoximines, e.g. I and II, in good to high yields.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Cho, Gae Young’s team published research in Journal of Organic Chemistry in 2010-01-15 | CAS: 145026-07-9

Synthesis and palladium-catalyzed coupling reactions of enantiopure p-bromophenyl methyl sulfoximine. [Erratum to document cited in CA142:355003]. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 50578-18-2

On page 2347, Scheme 1 is incorrect due to the wrong stereochem. assignment of compound 5 thereby making the configuration of Compound 6 incorrect as well; the correct version of Scheme 1 is given. Sulfoximine 2 as well as all subsequent mols. derived thereof should have the R-configuration at sulfur.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem