- Catalyst-Free Electrophilic Ring Expansion of N-Unprotected Aziridines with α-Oxoketenes to Efficient Access 2-Alkylidene-1,3-Oxazolidines
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2-(2-Oxoalkylidene)-1,3-oxazolidine derivatives were synthesized in good to excellent yields regiospecifically through the catalyst-free electrophilic ring expansion of N-unprotected aziridines and the ketene C=O double bond of α-oxoketenes, in situ generated from the microwave-assisted Wolff rearrangement of 2-diazo-1,3-diketones. The ring expansion predominantly underwent an SN1 process and the hydrogen bond decides the (E)-configuration of products. (Figure presented.).
- Chen, Xingpeng,Huang, Zhengshuo,Xu, Jiaxi
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supporting information
p. 3098 - 3108
(2021/05/10)
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- Construction of isoxazolone-fused phenanthridinesviaRh-catalyzed cascade C-H activation/cyclization of 3-arylisoxazolones with cyclic 2-diazo-1,3-diketones
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A Rh(iii)-catalyzed cascade C-H activation/intramolecular cyclization of 3-aryl-5-isoxazolones with cyclic 2-diazo-1,3-diketones was described, leading to the formation of isoxazolo[2,3-f]phenanthridine skeletons. The protocol features the simultaneous one-pot formation of two new C-C/C-N bonds and one heterocycle in moderate-to-good yields with good functional group compatibility. It is amenable to large-scale synthesis and further transformation.
- Hu, Wangcheng,He, Xinwei,Zhou, Tongtong,Zuo, Youpeng,Zhang, Shiwen,Yang, Tingting,Shang, Yongjia
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supporting information
p. 552 - 556
(2021/02/06)
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- Rhodium-Catalyzed [4+2] Annulation of N-Aryl Pyrazolones with Diazo Compounds To Access Pyrazolone-Fused Cinnolines
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An efficient synthesis of novel dinitrogen-fused heterocycles such as pyrazolo[1,2-a]cinnoline derivatives have been accomplished by the rhodium(III)-catalyzed reaction of N-arylpyrazol-5-ones with α-diazo compounds. This reaction proceeds through a cascade C?H activation/intramolecular cyclization with a broad substrate scope. Furthermore, this protocol is successfully extended to the unusual phosphorus-containing α-diazo compounds and cyclic diazo compounds as the cross-coupling partners to deliver the two new kinds of pyrazolo[1,2-a]cinnolinones. The control experiments were performed to reveal insight into the mechanism of this reaction, involving reversible C?H activation, migratory insertion of the diazo compound, and cascade cyclization as the key steps of the transformation. Moreover, gram-scale synthesis and further transformation of the target product demonstrate the synthetic utility of the present protocol.
- Dhole, Sandip,Huang, Wan-Wen,Huang, Ying-Ti,Lin, Chih-Yu,Sun, Chung-Ming
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supporting information
p. 4984 - 4992
(2021/09/28)
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- A 'sulfonyl-azide-free' (SAFE) aqueous-phase diazo transfer reaction for parallel and diversity-oriented synthesis
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Diazo transfer reactions are notoriously associated with the use of potentially explosive sulfonyl azides. The first 'sulfonyl-azide-free' (SAFE) protocol for producing diazo compounds from their active-methylene precursors via the Regitz diazo transfer reaction was developed and has displayed a remarkable substrate scope. It can be applied to generating arrays of diazo compounds for further evolution via combinatorial chemistry and a range of scaffold-generating transformations.
- Dar'In, Dmitry,Kantin, Grigory,Krasavin, Mikhail
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supporting information
p. 5239 - 5242
(2019/05/08)
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- Regioselective synthesis of highly functionalized furans through the RuII-catalyzed [3+2] cycloaddition of diazodicarbonyl compounds
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A novel method for the RuII-catalyzed regioselective synthesis of highly functionalized furans from readily available cyclic and acyclic diazodicarbonyl compounds and terminal alkynes is described. The devised protocol offers a straightforward means to the construction of a variety of diverse furan derivatives through powerful cascade processes, including the formation of ruthenium carbenoid, cyclopropenation, ring-opening metathesis, and cyclization. Copyright
- Xia, Likai,Lee, Yong Rok
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p. 3430 - 3442
(2014/06/09)
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- Efficient one-pot synthesis of cyclic β-enaminoamides by thermal Wolff rearrangement of cyclic 2-diazo-1,3-dicarbonyls and conversion to uracil derivatives
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This paper describes simple and efficient approaches for the preparation of β-enaminoamides through thermal Wolff rearrangement of cyclic diazodicarbonyls followed by trapping with various amines. The synthesized β-enaminoamides were readily converted into uracil derivatives.
- Neupane, Pratik,Li, Xin,Jung, Jae Hak,Lee, Yong Rok,Kim, Sung Hong
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body text
p. 2496 - 2508
(2012/04/23)
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- Direct ionic liquid promoted organocatalyzed diazo-transfer reactions: diversity-oriented synthesis of diazo-compounds
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A practical and novel ionic liquid promoted organocatalytic selective diazo-transfer process for the synthesis of highly substituted diazo-compounds in high yields is reported. The ionic liquid can be reused without affecting the reaction rates or yields over five runs.
- Ramachary, Dhevalapally B.,Narayana, Vidadala V.,Ramakumar, Kinthada
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p. 2704 - 2709
(2008/09/19)
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- The reactions of diazo compounds with lactones. Part 2. The reaction of cyclic 2-diazo-1,3-dicarbonyl compounds with diketene: Benzofuran formation
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Cyclic 2-diazo-1,3-dicarbonyl compounds react with diketene in the presence of rhodium(II) salts to give benzofurans as the major isolated products. The formation of intermediate products with exocyclic double bonds which isomerise to benzofurans provides support for the proposed mechanism which involves initial formation of a dioxaspirooctenone by a formal dipolar cycloaddition reaction of a carbenoid to the exocyclic double bond of diketene followed by the loss of carbon dioxide. Acyclic 2-diazo-1,3-dicarbonyl compounds give furans in poor yield.
- Murphy, Paul V.,O'Sullivan, Timothy J.,Kennedy, Bryan D.,Geraghty, Niall W.A.
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p. 2121 - 2126
(2007/10/03)
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- Synergistic insecticidal compositions containing dione esters
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Insecticidal compositions are provided which contain dione esters in admixture with other insecticides such as pyrethroid, carbamate or organophosphates. The use of the compositions of this invention provides synergistic kill of insects.
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- Biocidal 2-aryl-1,3-cyclohexane dione compounds and alkali metal and ammonium salts thereof
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2-Aryl-1,3-cyclohexanedione compounds and their alkali metal and ammonium salts exhibit outstanding herbicidal, miticidal and mite ovicidal activity.
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- Method of controlling acarina ectoparasites on warmblooded animals by orally administering to the animal an ectoparasitically effective amount of a 2-aryl-1,3-cyclohexanedione compound, and alkali metal salts, ammonium salts and enol esters thereof
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A method of controlling acarina ectoparasites on warmblooded animals by orally administering to the animals an ectoparasitically effective amount of a 2-aryl-1,3-cyclohexanedione compound and alkali metal salts, ammonium salts and enol ester derivative thereof.
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