M.W=150-200 | Page 5 of 11 | Heterocyclic Building Blocks-Benzoxazole

Kong, Xianqiang’s team published research in Journal of Organic Chemistry in 2021-10-01 | CAS: 1621962-30-8

Electrochemical Oxidative C(sp3)-H/N-H Coupling of Diarylmethanes with Sulfoximines or Benzophenone Imine. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

4-(S-Methylsulfonimidoyl)benzonitrile (BD00975057) 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 efficient electrochem. method for the synthesis of N-alkylated sulfoximines I [R = Ph, 2-BrC6H4, 4-MeOC6H4, etc.; R1 = Me, Et, n-Bu, Ph, 4-MeC6H4; Ar1 = Ph, 4-FC6H4, 4-ClC6H4; Ar2 = Ph, 4-FC6H4] by electrochem. oxidative C(sp3)-H/N-H coupling of sulfoximines and diarylmethanes was developed. In addition, used the same conditions for electrochem. dehydrogenative amination of diarylmethanes with benzophenone imine as an aminating agent to obtain II [Ar3 = Ph, 4-MeC6H4, 4-FC6H4; Ar4 = Ph, 4-MeC6H4, 4-FC6H4, 4-ClC6H4]. The reactions showed good functional group tolerance and afforded the corresponding products in moderate to good yields without the use of a stoichiometric oxidant, a metal catalyst, or an activating agent.

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

(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.

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

Xu, Jian’s team published research in Organic Chemistry Frontiers in 2017 | CAS: 1621962-30-8

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/50578-18-2.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

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

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

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

Shankar, Majji’s team published research in Chemical Science in 2020 | CAS: 4381-25-3

Double annulation of ortho- and peri-C-H bonds of fused (hetero)arenes to unusual oxepino-pyridines. Recommended basis is Sulfoximine, Bioisosteric. Products is: https://www.ambeed.com/products/50578-18-2.html, 145026-07-9

Direct difunctionalization of chem. distinct ortho- and peri-C-H bonds of fused hetero(arenes) was illustrated through an unusual one-pot domino {[4 + 2] and [5 + 2]} double annulation with alkynes for the first time. This process was viable under Ru(II)-catalysis using a sulfoximine directing group and builds four bonds [(C-C)-(C-N) and (C-C)-(C-O)] in a single operation. Such synthetic manifestation offers access to uncommon [6,7]-fused oxepino-pyridine skeletons, e.g., I. DFT calculations provided mechanistic insight into this double annulation of naphthoic acid derivatives with alkynes and corroborate the participation of a ruthena-oxabicyclooctene intermediate, which was responsible for the rare 7-membered ring formation.

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

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

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