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

Li, Zhen’s team published research in Organic Letters in 2019-05-03 | CAS: 50578-18-2

Organocatalytic Synthesis of Sulfoximidoyl-Containing Carbamates from Sulfoximines and Morita-Baylis-Hillman Carbonates. 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.

An unexpected substitution reaction providing sulfoximidoyl-containing carbamates was observed when Morita-Baylis-Hillman carbonates and NH-sulfoximines were mixed in acetonitrile at elevated temperature Key ingredients were triethylamine and ortho-hydroxybenzoic acid, which both had to be present in catalytic quantities.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Ried, Walter’s team published research in Synthesis in 1987-10-31 | CAS: 50578-18-2

New thienothiadiazines and pyridothiadiazines from N-cyanoimidates and sulfoximides. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

Condensation of Nú·CN:CRR1 (R = OMe, OEt, SMe; R1 = Ph, 4-MeC6H4, 4-ClC6H4, 2-thienyl, SMe, 2-furyl, Me) with HNS(O)R2R3 [R2 = R3 = Me; R2R3 = (CH2)4] gave 27-91% Nú·CN:CR1N:S(O)R2R3 (I). Substitution reaction of I [R1 = SMe, R2 = R3 = Me, R2R3 = (CH2)4] with pyrrolidine gave 60-86% I (R1 = 1-pyrrolidinyl) whereas, cyclocondensation with HSCH2CO2Me gave 50-64% thiazolylsulfoximide II. NaH-catalyzed cyclization of I gave 29-74% thienothiadiazine oxides III (R1 = Ph, 4-MeC6H4, 4-ClC6H4, 2-thienyl, 1-pyrrolidinyl) and 33-57% pyrimidothiadiazine oxides IV (R1 = Ph, 4-MeC6H4, 4-ClC6H4, 2-thienyl).

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Johnson, Carl R.’s team published research in Journal of Organic Chemistry in 1989-02-17 | CAS: 50578-18-2

Preparation of free sulfoximines by treatment of N-tosylsulfoximines with sodium anthracenide. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

A solution of sodium anthracenide in DME was added dropwise to a stirred solution or suspension of N-tosylsulfoximes RR1S(O):NTs [I; Ts = tosyl, R = R1 = Me, Bu; R = Me, R1 = morpholino, Bu2N; RR1 = (CH2)4] in DMF under argon at 0¡ã to afford 68-98% sulfoximines RR1S(O):NH. I (R = Et, R1 = MeCCl2) gave S,S-diethylsulfoximine; I (R = Me, R1 = Ph, PhCH2) were unreactive.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Yang, Qingjing’s team published research in Journal of Organic Chemistry in 2018-09-21 | CAS: 50578-18-2

Palladium-Catalyzed N-Arylation of Sulfoximines with Aryl Sulfonates. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

Palladium-catalyzed C-N bond coupling reaction between NH-sulfoximines and aryl halides (e.g., -Br, -I, and -Cl and pseudohalides -OTf and -ONf) was successfully achieved. Nevertheless, aryl tosylates/mesylates left much to be achieved. In this report, a general N-arylation of sulfoximines with aryl sulfonates is described. Using Pd(OAc)2/MeO-CM-phos complex, the N-aryl sulfoximine products can be obtained in good-to-excellent yields (up to 99%) with good common functional group compatibility. In addition to arene moieties, alkenyl tosylates are shown to be successful coupling partners.

Palladium-Catalyzed N-Arylation of Sulfoximines with Aryl Sulfonates. 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

Pimpasri, Chaleena’s team published research in Organic & Biomolecular Chemistry in 2017 | CAS: 50578-18-2

Copper-catalyzed oxidative decarboxylative coupling of ¦Á-keto acids and sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

A copper-catalyzed oxidative decarboxylative coupling of ¦Á-keto acids with NH-sulfoximines has been developed. With CuBr as the catalyst and K2S2O8 as the oxidant, this reaction enables the formation of a C-N bond and gives N-aroylsulfoximine products in moderate to excellent yields. The reaction mechanism is likely to involve the generation of a reactive aroyl radical intermediate.

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Wang, Long’s team published research in Angewandte Chemie, International Edition in 2013 | CAS: 50578-18-2

Copper-catalyzed oxidative cross-coupling of sulfoximines and alkynes. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

N-Alkynylation and N-acylation of sulfoximines R1R2S(O):NH was achieved by copper dichloride-catalyzed oxidative coupling with ¦Á-alkynes with optional hydrolysis on silica. N-Alkynyl sulfoximines R1R2S(O):NCú·CAr [2b-l; R1 = Ph, R2 = Me; R1-R2 = (CH2)4; Ar = Ph, 2-MeC6H4, 3-pyridinyl, 4-XC6H4, X = CN, NO2, F, Me, OMe] were prepared by reaction of R1R2S(O):NH [1a-c, R1, R2: Ph, Me; Me, Me; (CH2)4] in a 2:1 M excess to alkynes HCú·CAr, HCú·CSiMe3 in pyridine as a solvent in the presence of 10 mol% of CuCl2, 2 equiv ov Na2CO3 and 1 atm of O2 with subsequent purification on triethylamine-deactivated silica gel. The hydrolysis products, N-(arylacetyl)sulfoximines R1R2S(O):NCOCH2Ar (6a-d; R1 = Ph, Me; R2 = Me; Ar = Ph, 4-NCC6H4, 4-NO2C6H4) were prepared by alkynylation with subsequent chromatog. on non-deactivated silica.

Copper-catalyzed oxidative cross-coupling of sulfoximines and alkynes. 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

Wang, Long’s team published research in Advanced Synthesis & Catalysis in 2013 | CAS: 50578-18-2

The Copper-Catalyzed Oxidative N-Acylation of Sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

An oxidative cross-coupling reaction between aldehydes and sulfoximines involving dual C-H/N-H functionalization was developed. This reaction process is facilitated by a simple copper catalyst (1 mol% loading) and tert-Bu hydroperoxide (TBHP) as the oxidant and proceeds under mild reaction conditions to afford a series of valuable N-acylated sulfoximine derivatives in excellent yields.

The Copper-Catalyzed Oxidative N-Acylation of Sulfoximines. 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

Tota, Arianna’s team published research in Chemical Communications (Cambridge, United Kingdom) in 2017 | CAS: 50578-18-2

Synthesis of NH-sulfoximines from sulfides by chemoselective one-pot N- and O-transfers. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

Direct synthesis of NH-sulfoximines from sulfides were achieved through O and NH transfer in the same reaction, occurring with complete selectivity. The reaction was mediated by bisacetoxyiodobenzene under simple conditions and employs inexpensive N-sources. Preliminary studies indicated that NH-transfer was likely to be first, followed by oxidation, but the reaction proceedes successfully in either order. A wide range of functional groups and biol. relevant compounds were tolerated. The use of AcO15NH4 affords 15N-labeled compounds

Referemce:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Jiang, Wenlong’s team published research in Science China: Chemistry in 2019-09-30 | CAS: 50578-18-2

Visible light promoted synthesis of N-aroylsulfoximines by oxidative C-H acylation of NH-sulfoximines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/1621962-30-8.html, 145026-07-9

The visible light-promoted synthesis of N-aroylsulfoximines was accomplished via an oxidative dehydrogenative coupling at room temperature under air without the addition of a photosensitizer, metal catalyst or base. This process exhibited good functional group tolerance, allowed facile isolation and purification and afforded N-aroylsulfoximines with high efficiency. The efficiency of the newly developed protocol was described in detail with 27 examples with yields ranging from 80% to 96%. Furthermore, the chirality of the NH-sulfoximine was completely maintained in the desired N-aroylsulfoximine product (< 99% ee). Visible light promoted synthesis of N-aroylsulfoximines by oxidative C-H acylation of NH-sulfoximines. 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

Xu, Jian’s team published research in Organic Chemistry Frontiers in 2017 | CAS: 50578-18-2

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/1621962-30-8.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