Syntheses of Anomeric Pairs of New C-Nucleosides via 1,3-Dipolar Cycloaddition Reaction, Part II

1997 ◽  
Vol 52 (11) ◽  
pp. 1393-1400 ◽  
Author(s):  
Zahida Maqboor ◽  
Mashooda Hasan ◽  
Kevin T. Potts ◽  
Abdul Malik ◽  
Tanveer Ahmad Nizami ◽  
...  
Keyword(s):  
Comparative Study ◽  
Spectral Data ◽  
Cycloaddition Reaction ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Reasonable Degree ◽  
Subsequent Hydrolysis

Abstract 1,3-Dipolar cycloaddition of dipolarophiles (1) and (2) with endocyclic heterocyclic azomethine ylides (4), (14) and (24), prepared in situ, leads to the protected β-and α-C-nucleo-sides (7), (8), (17), (18), (27) and (28), respectively. These, on subsequent hydrolysis, provide the corresponding C-nucleosides. The structures of all the synthesized com pounds are con­ firmed through analytical and spectral data. The assignment of configuration at C -1′ position of the C-nucleosides could be done by a comparative study of the properties of the corre­sponding α and β anomers with a reasonable degree of certainity.

A Convenient Synthesis of Fused Tetrahydroazocines from Acenaphthylene-1,2-dione, Proline, and Acetylenic Esters

Synlett ◽  
2017 ◽  
Vol 29 (05) ◽  
pp. 635-639 ◽  
Author(s):  
Issa Yavari ◽  
Leila Baoosi ◽  
Mohammad Halvagar
Keyword(s):  
Cycloaddition Reaction ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
X Ray Diffraction ◽  
Acetylenic Esters ◽  
X Ray ◽  
Convenient Synthesis ◽  
Boat Form ◽  
Twist Boat

A synthesis of dialkyl (12E,14E)-7-oxo-10,11-dihydro-7H,9H-azocino[2,1-a]benzo[de]isoquinoline-13,14-dicarboxylates through a 1,3-dipolar cycloaddition reaction of azomethine ylides, generated in situ from proline and acenaphthylene-1,2-dione, with dialkyl acetylenedicarboxylates is described. According to the X-ray diffraction data, the tetrahydroazocine ring has a rigid twist-boat form with approximate local C2 symmetry.

scholarly journals Multicomponent synthesis of spiropyrrolidine analogues derived from vinylindole/indazole by a 1,3-dipolar cycloaddition reaction

2016 ◽  
Vol 12 ◽  
pp. 2893-2897 ◽  
Author(s):  
Manjunatha Narayanarao ◽  
Lokesh Koodlur ◽  
Vijayakumar G Revanasiddappa ◽  
Subramanya Gopal ◽  
Susmita Kamila
Keyword(s):  
Amino Acids ◽  
Cycloaddition Reaction ◽  
Thermal Conditions ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Side Chains ◽  
Multicomponent Synthesis ◽  
One Pot ◽  
Cyclic Adducts

A new series of spiropyrrolidine compounds containing indole/indazole moieties as side chains have been accomplished via a one-pot multicomponent synthesis. The method uses the 1,3-dipolar cycloaddition reaction between N-alkylvinylindole/indazole and azomethine ylides, prepared in situ from cyclic/acyclic amino acids. The 1,3-dipolar cycloaddition proceeds efficiently under thermal conditions to afford the regio- and stereospecific cyclic adducts.

Syntheses of Anomeric Pairs of New C-Nucleosides via 1,3-Dipolar Cycloaddition Reaction, Part I

1997 ◽  
Vol 52 (11) ◽  
pp. 1383-1392 ◽  
Author(s):  
Zahida Maqbool ◽  
Mashooda Hasan ◽  
Kevin T. Pott ◽  
Abdul Malik ◽  
Tanveer Ahmad Nizami ◽  
...  
Keyword(s):  
Comparative Study ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Reasonable Degree

Abstract A convenient pathway to a variety of β-and α-C-nucleosides has been developed by utilizing 1,3-dipolar cycloaddition reactions of various exocyclic and endocyclic heterocyclic ylides with β (5a) and α (5b) anomers of ethyl 3-(2′,3′-O-isopropylidene-5′-O-trityl-D-ribofurano-syl) propiolate, respectively. Assignment of configuration at exposition of the C-nucleosides could be made by a comparative study of the properties of corresponding α and β anomers with a reasonable degree of certainity.

scholarly journals Copper–phenanthroline catalysts for regioselective synthesis of pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and of pyrrolo[1,2-a]phenanthrolines under mild conditions

2014 ◽  
Vol 10 ◽  
pp. 692-700 ◽  
Author(s):  
Rupankar Paira ◽  
Tarique Anwar ◽  
Maitreyee Banerjee ◽  
Yogesh P Bharitkar ◽  
Shyamal Mondal ◽  
...  
Keyword(s):  
Catalytic System ◽  
Cycloaddition Reaction ◽  
Regioselective Synthesis ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
General Applicability ◽  
Mild Conditions ◽  
Stabilized Azomethine Ylides ◽  
High Yields

A new series of pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and pyrrolo[1,2-a]phenanthrolines were efficiently built up from an 8-hydroxyquinoline derivative or phenanthroline via 1,3-dipolar cycloaddition reaction involving non-stabilized azomethine ylides, generated in situ from the parent furo[3,2-h]quinoliniums/phenanthroliums, in presence of a copper(II) chloride–phenanthroline catalytic system. The methodology combines general applicability with high yields.

scholarly journals Dearomative [3 + 2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides

RSC Advances ◽  
2020 ◽  
Vol 10 (48) ◽  
pp. 28720-28724 ◽  
Author(s):  
Kai-Kai Wang ◽  
Yan-Xin Xie ◽  
Yan-Li Li ◽  
Rongxiang Chen ◽  
Zhan-Yong Wang
Keyword(s):  
Efficient Method ◽  
Cycloaddition Reaction ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition

A simple and efficient method for the synthesis of benzo[4,5]thieno[2,3-c]pyrroles via dearomative [3 + 2] 1,3-dipolar cycloaddition reaction of nitrobenzothiophenes with an in situ-generated nonstabilized azomethine ylides have been developed.

Bifunctional AgOAc/ThioClickFerrophos catalyzed asymmetric 1,3-dipolar cycloaddition reaction of azomethine ylides to nitroalkenes

Tetrahedron ◽  
2016 ◽  
Vol 72 (21) ◽  
pp. 2666-2670 ◽  
Author(s):  
Midori Kimura ◽  
Yukiko Matsuda ◽  
Akihiro Koizumi ◽  
Chihiro Tokumitsu ◽  
Yuichiro Tokoro ◽  
...  
Keyword(s):  
Cycloaddition Reaction ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition

scholarly journals Green ultrasound-assisted three-component click synthesis of novel 1H-1,2,3-triazole carrying benzothiazoles and fluorinated-1,2,4-triazole conjugates and their antimicrobial evaluation

2017 ◽  
Vol 67 (3) ◽  
pp. 309-324 ◽  
Author(s):  
Nadjet Rezki ◽  
Mohamed Reda Aouad
Keyword(s):  
Antimicrobial Activity ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Terminal Alkynes ◽  
One Pot ◽  
Alkyl Aryl ◽  
Antimicrobial Evaluation ◽  
Ultrasound Assisted ◽  
Click Synthesis

AbstractThe present study describes an efficient and ecofriendly, ultrasound, one-pot click cycloaddition approach for the construction of a novel series of 1,4-disubstituted-1,2,3-triazoles tethered with fluorinated 1,2,4-triazole-benzothiazole molecular conjugates. It involved three-component condensation of the appropriate bromoacetamide benzothiazole, sodium azide and 4-alkyl/aryl-5-(2-fluorophenyl)-3-(prop-2-ynylthio)-1,2,4-triazoles4a-ethrough a Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction. This approach involvesin situgeneration of azidoacetamide benzothiazole, followed by condensation with terminal alkynes in the presence of CuSO4/Na-ascorbate in aqueous DMSO under both conventional and ultrasound conditions. Some of the designed 1,2,3-triazole conjugates6a-owere recognized for their antimicrobial activity against some bacterial and fungal pathogenic strains.

Organocatalytic Enantioselective [3+2] Cycloaddition of Azomethine Ylides and Acrolein

2015 ◽  
Vol 2 (1) ◽  
Author(s):  
Iratxe Ugarriza ◽  
Uxue Uria ◽  
Efraím Reyes ◽  
Luisa Carrillo ◽  
Jose L. Vicario
Keyword(s):  
Secondary Amine ◽  
Cycloaddition Reaction ◽  
Azomethine Ylides ◽  
Optimum Conditions

AbstractThe [3+2]-cycloaddition reaction between acrolein and in situ generated acyclic azomethine ylides promoted by a chiral secondary amine to generate C-3 unsubstituted pyrrolidines has been studied in detail. Optimum conditions involve the use of the cheap and readily available l-Proline as catalyst to afford the pyrrolidine cycloadduct with complete diastereomeric control and up to 80% enantiomeric control.

Catecholated graphene-filled polyimide with enhanced mechanical, thermal, and tribological properties

2020 ◽  
pp. 095400832094035
Author(s):  
Xing Wu ◽  
Zhengyu Jin ◽  
Yuejin Zhu ◽  
Haichao Zhao
Keyword(s):  
Friction And Wear ◽  
In Situ Polymerization ◽  
Cycloaddition Reaction ◽  
Mechanical Analysis ◽  
Dipolar Cycloaddition ◽  
Wear Properties ◽  
Comprehensive Properties ◽  
Transmission Electron ◽  
Friction And Wear Tests

In order to achieve good dispersion of graphene in polyimide (PI), catecholated graphene (G-Cat) was prepared by 1,3-dipolar cycloaddition reaction of N-methylglycine and 3,4-dihydroxybenzaldehyde with graphene sheets. G-Cat/PI composites were prepared by in situ polymerization with pyromellitic dianhydride and 4,4-oxydianiline in the presence of G-Cat. The successful modification of graphene was proved by infrared spectroscopy, Raman spectroscopy, and transmission electron microscopy. The comprehensive properties of G-Cat/PI composites were studied by tensile, dynamic mechanical analysis, thermogravimetric analysis, and friction and wear tests. By observing the morphology of wear marks, the friction and wear properties of the composites were emphatically analyzed. Therefore, graphene/PI composites were expected to have broad application prospects in lubrication and wear resistance.

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