Synthesis of spirocyclic oxazole derivatives from 2-arylidene cycloalkanones and α-halohydroxamates

Wan, Huiyang; Xia, Shuangshuang; Liu, Xinghua; Jian, Yongchan; An, Yuanyuan; Wang, Yubin

doi:10.1039/d2ob00701k

Cited by 7 publications

(2 citation statements)

References 62 publications

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“…Additionally, the potential utility of the method was shown by gram scale reaction and synthetic transformation of desired products (Scheme 13). [27] …”

Section: Cycloaddition Reactions Involving Aza‐oxyallyl Cations As Th...mentioning

confidence: 99%

“…Additionally, the potential utility of the method was shown by gram scale reaction and synthetic transformation of desired products (Scheme 13). [27] Two heteroatoms (S and N) containing group of heterocycles Rhodanines (49) and its derivatives were synthesized from common solvent carbon sulfide and in-situ generated azaoxyallyl cation via (3 + 2) cycloaddition with K 2 CO 3 in THF was reported by Shi and group in 2022. Different α-halohydroxamates were well designed and desired product was obtained in good to excellent yield except for α,α-dimethyl-α-bromohydroxamates where trace amount of desired product was obtained and with α,α-dichlorohydroxamates no desired product was seen.…”

Section: [3 + 2]-cycloaddition Reactionsmentioning

confidence: 99%

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Aza‐oxyallyl Cations and Their Applications in (3+m) Cycloaddition Reactions

Deeksha

Singh

2022

Eur J Org Chem

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Aza‐oxyallyl cations, as proposed by Sheehan in the 1960s have garnered significant attention among the synthetic organic community, owing to their diverse reactivity profile for constructing N‐scaffolds of biological interest. During its initial growth, aza‐oxyallyl cations were used effectively as a 3‐unit synthon as 1,3 dipoles to create N‐heterocycles via cycloaddition reactions, wherein aza‐oxyallyl cation served as electrophilic counterpart. Recently, new variations of aza‐oxyallyl cations reactivity have been reported, including its usage as a 1,4 dipole in cycloaddition reactions, domino reactions, and the unique alkylating ability of heteroatoms. This review article provides an update of the recent developments in this area and the prevailing mechanistic insight.

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“…Additionally, the potential utility of the method was shown by gram scale reaction and synthetic transformation of desired products (Scheme 13). [27] …”

Section: Cycloaddition Reactions Involving Aza‐oxyallyl Cations As Th...mentioning

confidence: 99%

Section: [3 + 2]-cycloaddition Reactionsmentioning

confidence: 99%

Aza‐oxyallyl Cations and Their Applications in (3+m) Cycloaddition Reactions

Deeksha

Singh

2022

Eur J Org Chem

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Base‐Promoted [4+3] Cycloadditions of N‐Thioacylimines with α‐Chlorohydroxamates: Construction of 1,3,5‐Thiadiazepin‐6(7H)‐One Derivatives

Liu,

Shao,

et al. 2024

Adv Synth Catal

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A metal‐free base‐promoted [4+3] cycloaddition reaction of N‐thioacyl imines in situ generated from α‐amido sulfones with α‐chlorohydroxamates is described. The reaction facilitates the straightforward synthesis of 1,3,5‐thiadiazepin‐6(7H)‐one derivatives in 44~90% yields. Moreover, a gram‐scale reaction and product transformation were conducted, which further increased the diversity of products.

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α‐Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source

Nishikata

2024

ChemistryOpen

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This review introduces the synthetic organic chemical value of α‐bromocarbonyl compounds with tertiary carbons. This α‐bromocarbonyl compound with a tertiary carbon has been used primarily only as a radical initiator in atom transfer radical polymerization (ATRP) reactions. However, with the recent development of photo‐radical reactions (around 2010), research on the use of α‐bromocarbonyl compounds as tertiary alkyl radical precursors became popular (around 2012). As more examples were reported, α‐bromocarbonyl compounds were studied not only as radicals but also for their applications in organometallic and ionic reactions. That is, α‐bromocarbonyl compounds act as nucleophiles as well as electrophiles. The carbonyl group of α‐bromocarbonyl compounds is also attractive because it allows the skeleton to be converted after the reaction, and it is being applied to total synthesis. In our survey until 2022, α‐bromocarbonyl compounds can be used to perform a full range of reactions necessary for organic synthesis, including multi‐component reactions, cross‐coupling, substitution, cyclization, rearrangement, stereospecific reactions, asymmetric reactions. α‐Bromocarbonyl compounds have created a new trend in tertiary alkylation, which until then had limited reaction patterns in organic synthesis. This review focuses on how α‐bromocarbonyl compounds can be used in synthetic organic chemistry.

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Synthesis of spirocyclic oxazole derivatives from 2-arylidene cycloalkanones and α-halohydroxamates

Abstract: Herein we disclose a facil route to spirocyclic oxazole derivatives via the [3 + 2] cycloaddition reactions between 2-arylidene cycloalkanones and azaoxyallyl cations which formed in situ from α-halohydroxamates in...

Cited by 7 publications

References 62 publications

Aza‐oxyallyl Cations and Their Applications in (3+m) Cycloaddition Reactions

Aza‐oxyallyl Cations and Their Applications in (3+m) Cycloaddition Reactions

Base‐Promoted [4+3] Cycloadditions of N‐Thioacylimines with α‐Chlorohydroxamates: Construction of 1,3,5‐Thiadiazepin‐6(7H)‐One Derivatives

α‐Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source

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