Lewis base catalyzed ring-expansion of isatin with 2,2,2-trifluorodiazoethane (CF3CHN2): An efficient route to 3-hydroxy-4-(trifluoromethyl)quinolinones

Lv, Shuaipeng; Sun, Yukun; Xu, Yilin; Yang, Shihai; Wang, Lei

doi:10.1016/j.cclet.2019.11.027

Cited by 10 publications

(2 citation statements)

References 41 publications

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“…Independently, Yang, Wang, and co-workers recently performed the reaction of isatines with in situ generated CF 3 CHN 2 (1), catalyzed by DBU. 88 The same year, Cahard performed similar studies on activated imines, using a chiral Bronsted acid 260 instead of BF 3 •Et 2 O (Scheme 52). 90 Activated imine 261 (and seven others) reacted with CF 3 CHN 2 to form the optically pure cis-aziridine 257 (99% ee) in 65% yield.…”

Section: Reaction With H + (Protonation)mentioning

confidence: 99%

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2,2,2-Trifluorodiazoethane (CF₃CHN₂): A Long Journey since 1943

Mykhailiuk

2020

Chem. Rev.

144

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2,2,2-Trifluorodiazoethane (CF3CHN2) has been proven to be a valuable reagent for the rapid synthesis of various classes of trifluoromethyl-substituted organic molecules in both academic and industrial research. The reagent was prepared first in 1943, but only recently it received a great attention from the scientific community. Protocols for in situ generation, in flow generation, and crystalline analogues of CF3CHN2 were developed during the past decade and have led to an ever-increasing number of publications on the topic. The current review summarizes and comprehensively analyzes all manuscripts in a peer-reviewed literature on 2,2,2-trifluorodiazoethane since its discovery in 1943 until today (as of 19 June 2020). These include contributions mostly overseen by scientific community before. A particular emphasis of this review is to classify the existing reactivity modes of CF3CHN2 and to systematically analyze the corresponding reaction mechanisms in details. At the end of this review, several undeveloped areas for CF3CHN2 are outlined, based on the overseen precedents in the literature.

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Section: Reaction With H + (Protonation)mentioning

confidence: 99%

“…Independently, Yang, Wang, and co-workers recently performed the reaction of isatines with in situ generated CF 3 CHN 2 ( 1 ), catalyzed by DBU . Even though the reaction gave the same products, it presumably proceeded via a different mechanism (via intermediate 116 on Scheme ).…”

Section: Reactions As C-nucleophilementioning

confidence: 99%

2,2,2-Trifluorodiazoethane (CF₃CHN₂): A Long Journey since 1943

Mykhailiuk

2020

Chem. Rev.

144

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Metal‐Free Photocyclization/Oxidation Cascade Constructing Quinoline‐2‐ones and Tetrahydrocarbazolones

Hao,

Huang

2024

Adv Synth Catal

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We reported a one‐pot photocyclization/ oxidation cascade of N‐aryl acrylamides to afford quinoline‐2‐ones. Thioxanthone was used as a bifunctional energy transfer agent to mediate both photocyclization and generation of singlet oxygen, the latter facilitates the dehydrogenation of dihydroquinoline‐2‐one intermediate. This cascade strategy also supports the 5‐endo‐trig cyclization to synthesize tetrahydrocarbazolones from phenylamino cyclohexenones.

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Sequential Nucleophilic Addition and Regioselective Ring‐Expansion Reactions of α‐Diazophosphonates with Isatins: Access to 4‐Phosphonylated‐3‐hydroxyquinolin‐2(1H)‐ones

Wang

Zhao²,

Bai

et al. 2022

Asian J Org Chem

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A sequential protocol of α-diazophosphonates with isatins to access a series of α-diazo-β-hydroxyphosphonate derivatives via the inorganic base catalysis was reported. The resulting α-diazo-β-hydroxyphosphonates could then be readily transformed to 4-phosphonylated-3-hydroxyquinolin-2(1H)-ones with moderate to excellent yields through a catalyst-free regioselective ring-expansion rearrangement.Control experiment demonstrates that intramolecular cyclization pathway is more reasonable for the ring-expansion process. In addition, a benzo[b]thiophene-derived isatin featured with the inhibition of SARS-CoV M pro was also suitable for this transformation and generated the corresponding scaffolds with potential anti-virus activities for further development.

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Lewis base catalyzed ring-expansion of isatin with 2,2,2-trifluorodiazoethane (CF3CHN2): An efficient route to 3-hydroxy-4-(trifluoromethyl)quinolinones

Cited by 10 publications

References 41 publications

2,2,2-Trifluorodiazoethane (CF₃CHN₂): A Long Journey since 1943

2,2,2-Trifluorodiazoethane (CF₃CHN₂): A Long Journey since 1943

Metal‐Free Photocyclization/Oxidation Cascade Constructing Quinoline‐2‐ones and Tetrahydrocarbazolones

Sequential Nucleophilic Addition and Regioselective Ring‐Expansion Reactions of α‐Diazophosphonates with Isatins: Access to 4‐Phosphonylated‐3‐hydroxyquinolin‐2(1H)‐ones

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Lewis base catalyzed ring-expansion of isatin with 2,2,2-trifluorodiazoethane (CF3CHN2): An efficient route to 3-hydroxy-4-(trifluoromethyl)quinolinones

Cited by 10 publications

References 41 publications

2,2,2-Trifluorodiazoethane (CF3CHN2): A Long Journey since 1943

2,2,2-Trifluorodiazoethane (CF3CHN2): A Long Journey since 1943

Metal‐Free Photocyclization/Oxidation Cascade Constructing Quinoline‐2‐ones and Tetrahydrocarbazolones

Sequential Nucleophilic Addition and Regioselective Ring‐Expansion Reactions of α‐Diazophosphonates with Isatins: Access to 4‐Phosphonylated‐3‐hydroxyquinolin‐2(1H)‐ones

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2,2,2-Trifluorodiazoethane (CF₃CHN₂): A Long Journey since 1943

2,2,2-Trifluorodiazoethane (CF₃CHN₂): A Long Journey since 1943