Chemodivergent Synthesis of Aza-Heterocycles with a Quarternary Carbon Center via [4 + 1] Annulation between Azoalkenes and α-Bromo Carbonyl Compounds

Zhang, Xiaoke; Wang, Haibo; Shu, Yan; Song, Gang; Zhang, Xuefang; Shao, Hongxia; Wang, Chaoyong

doi:10.1021/acsomega.2c04127

Cited by 4 publications

(2 citation statements)

References 55 publications

(23 reference statements)

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“…KOH-trigged 1,4-elimination of α-halo hydrazone 2a generated the 1,2-diazadiene intermediate Int 1 in situ. [16][17][18][19] The azomethine imine 1a then trapped the 1,2diazadiene intermediate Int 1 affording the tetrazepine derivative through continuous C-N bond formation.…”

Section: Resultsmentioning

confidence: 99%

Strategy to Construct Functionalized Tetrazepine Derivatives via [4+3] Annulation Reaction of Azomethine Imine with Azadiene Precursor

Zhang,

Zheng,

Wang

2023

Chinese Journal of Organic Chemistry

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Tetrazepine derivative exhibits good biological activities. Only a limited method has been devoted to constructing these frameworks to date. Therefore, an efficient and novel way was established for the synthesis of functionalized tetrazepine scaffolds through the cycloaddition reaction of azomethine imine with 1,2-azadiene formed in situ by α-halogeno hydrazones in the presence of KOH. This transformation shows excellent functional group tolerance and substrate scope.

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Section: Resultsmentioning

confidence: 99%

Strategy to Construct Functionalized Tetrazepine Derivatives via [4+3] Annulation Reaction of Azomethine Imine with Azadiene Precursor

Zhang,

Zheng,

Wang

2023

Chinese Journal of Organic Chemistry

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“…Pyrazolines 149 were formed by the reaction between DDs and α ‐bromo dicarbonyl compounds 148 . Not only malonate compounds, but also ethyl acetoacetate analogues were used, as shown in Scheme 28b [56c] . Formerly, Attanasi group, which has a longstanding interest in DDs chemistry, reported a strategy for the formation of mono‐, bi‐, and tricyclic pyrazolines.…”

Section: [4+1]‐cycloadditionsmentioning

confidence: 99%

Strategies and Methods for the Synthesis of 2‐Pyrazolines: Recent Developments (2012–2022)

Matiadis

2023

Adv Synth Catal

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2‐Pyrazolines are important five‐membered heterocycles, containing two adjacent nitrogen atoms. They can incorporate various functional groups and possess unique biological properties. Moreover, they have been used as useful building blocks. In recent years, the field of 2‐pyrazoline synthesis has experienced enormous progress. Novel strategies have been developed, and many studies reporting improvements or adaptations of existing protocols have been published, giving access to new functionalizations, unexplored structures, and/or enantioselective synthesis. This review summarizes the progress made in synthetic methodologies during the period from 2012 to 2022. The functionalization challenges and capabilities, scopes and limitations of the reactions, substitution patterns, and mechanisms of the reactions, where appropriate, will be discussed.

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Strategy to Construct Polycyclic Scaffolds via Formal Aza‐Diels‐Alder Reaction of Dihydro‐β‐Carboline with Heterodiene Precursor

et al. 2023

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Chemodivergent Synthesis of Aza-Heterocycles with a Quarternary Carbon Center via [4 + 1] Annulation between Azoalkenes and α-Bromo Carbonyl Compounds

Abstract: An efficient [4 + 1] annulation reaction between in situ generated azoalkene intermediates and α-bromocarbonyls has been established. A series of skeletally diverse aza-heterocycles with a functionalized quaternary center were obtained in up to 89% yield under mild conditions.

Cited by 4 publications

References 55 publications

Strategy to Construct Functionalized Tetrazepine Derivatives via [4+3] Annulation Reaction of Azomethine Imine with Azadiene Precursor

Strategy to Construct Functionalized Tetrazepine Derivatives via [4+3] Annulation Reaction of Azomethine Imine with Azadiene Precursor

Strategies and Methods for the Synthesis of 2‐Pyrazolines: Recent Developments (2012–2022)

Strategy to Construct Polycyclic Scaffolds via Formal Aza‐Diels‐Alder Reaction of Dihydro‐β‐Carboline with Heterodiene Precursor

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