Introducing chirality in halogenated 3-arylsydnones and their corresponding 1-arylpyrazoles obtained by 1,3-dipolar cycloaddition

Popa Marcel Mirel; Shova Sergiu; Hrubaru Madalina; Barbu Loredana; Draghici Constantin; Dumitrascu Florea; Dumitrescu Denisa E.

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Introducing chirality in halogenated 3-arylsydnones and their corresponding 1-arylpyrazoles obtained by 1,3-dipolar cycloaddition

机译：在卤化3- arylsydnones中引入手性和其相应的1-芳基吡唑由1,3-偶极环加装

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New 1-arylpyrazoles substituted with halogen atoms (Br, I) were synthesized from the corresponding sydnones by 1,3-dipolar cycloaddition. By introduction of a prochiral group such as isopropyl, in the ortho position of the benzene ring, in the starting phenylglycine 1 the rotamers caused by the hindered rotation between the phenyl and the heterocyclic ring were detected by NMR spectroscopy for 1-arylpyrazoles and for the first time for 3-arylsydnones. The N-nitrosophenylglycines present E-Z stereoisomerism due to the partial C-N double bond character. All the new compounds were structurally characterized by NMR spectroscopy and confirmed by X-ray crystallography. The crystal structures of N-nitrosophenylglycine 2c and of the sydnone 3c present similar BrMIDLINE HORIZONTAL ELLIPSISBr type II halogen contacts.

机译：用1,3-偶极环加装入从相应的Sydnones中合成了用卤素原子（Br，I）取代的新的1-芳基吡唑。通过引入诸如异丙基的胰岛丙基，在苯环的邻位，在起始苯基甘氨酸中，由苯基和杂环之间的受阻旋转引起的旋转变物被NMR光谱检测到1-芳基吡唑并用于第一次适用于3 arylsydnones。由于部分C-N双键特征，N-硝基苯基甘氨酸存在E-Z立体异构。所有新化合物都是通过NMR光谱的结构表征，并通过X射线晶体学证实。 N-硝基苯基甘氨酸2C和Sydnone 3C的晶体结构存在类似的BRMidline水平椭圆型II型卤素触点。

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《RSC Advances》 |2020年第27期|共9页
作者
Popa Marcel Mirel; Shova Sergiu; Hrubaru Madalina; Barbu Loredana; Draghici Constantin; Dumitrascu Florea; Dumitrescu Denisa E.;
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Romanian Acad Ctr Organ Chem CD Nenitzescu Spl Independentei 202B Bucharest 060023 Romania;

Petru Poni Inst Macromol Chem Aleea Gr Ghica Voda 41A Iasi 700487 Romania;

Romanian Acad Ctr Organ Chem CD Nenitzescu Spl Independentei 202B Bucharest 060023 Romania;

Romanian Acad Ctr Organ Chem CD Nenitzescu Spl Independentei 202B Bucharest 060023 Romania;

Romanian Acad Ctr Organ Chem CD Nenitzescu Spl Independentei 202B Bucharest 060023 Romania;

Romanian Acad Ctr Organ Chem CD Nenitzescu Spl Independentei 202B Bucharest 060023 Romania;

Ovidius Univ Constanta Fac Pharm Str Cpt Av Al Serbanescu 6 Campus Corp C Constanta 900470 Romania;

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正文语种 eng
中图分类化学;
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1. Introducing chirality in halogenated 3-arylsydnones and their corresponding 1-arylpyrazoles obtained by 1,3-dipolar cycloaddition [J] . Popa Marcel Mirel, Shova Sergiu, Hrubaru Madalina, RSC Advances . 2020,第27期

机译：在卤化3- arylsydnones中引入手性和其相应的1-芳基吡唑由1,3-偶极环加装
2. A facile access to 1,3,4-trisubstituted pyrazoles via 1,3-dipolar cycloaddition of 3-arylsydnones with α,β-unsaturated ketones [J] . Fei Chen, Fang-Ming Liu, Hai Shi Monatshefte fur Chemie . 2013,第6期

机译：通过3-芳基丁烯酮与α，β-不饱和酮的1,3-偶极环加成反应轻松获得1,3,4-三取代吡唑
3. Exclusive Formation of l-Aryl-3-(5-nitro-2-furyl)-4-aroylpyrazoles via Regiospecific 1,3-Dipolar Cycloaddition of 3-Arylsydnones with alpha,beta-Acetylenic Ketones [J] . Jyoti C.Hegde, Ganesha Rai, Vedavati G.Puranik, Synthetic Communications . 2006,第7a9期

机译：通过3-芳基sydnones与α，β-乙炔酮的区域特异性1,3-偶极环加成反应独家形成1-芳基-3-（5-硝基-2-呋喃基）-4-芳酰基吡唑
4. Asymmetric 1,3-Dipolar Cycloaddition by Means of Chiral Phosphoric Acid [C] . Yuan Jin, Takahiko Akiyama 日本化学会春季年会講演予稿集 . 2018

机译：通过手性磷酸不对称1,3-偶极环加装入
5. Design and Synthesis of Multivalent Mimotope Constructs via Cu(I)-Catalyzed Azide- Alkyne 1,3 Dipolar Cycloaddition as Potential HIV-1 Vaccine Candidates. [D] . Hoch, Jessica Anne. 2014

机译：通过铜（I）催化的叠氮化物-炔烃1,3双极环加成作为潜在的HIV-1疫苗候选对象，设计和合成多价模拟表位。
6. Green Protocols in Heterocycle Syntheses via 1,3-Dipolar Cycloadditions [O] . Katia Martina, Silvia Tagliapietra, Valery V. Veselov, 1970

机译：通过1,3-偶极环加成反应进行杂环合成中的绿色方案
7. Introducing chirality in halogenated 3-arylsydnones and their corresponding 1-arylpyrazoles obtained by 1,3-dipolar cycloaddition [O] . Marcel Mirel Popa, Sergiu Shova, Madalina Hrubaru, 2020

机译：在卤化3- arylsydnones中引入手性和其相应的1-芳基吡唑由1,3-偶极环加装

Introducing chirality in halogenated 3-arylsydnones and their corresponding 1-arylpyrazoles obtained by 1,3-dipolar cycloaddition

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