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.

Concise Synthesis of Tryptanthrin Spiro Analogues with In Vitro Antitumor Activity Based on One-Pot, Three-Component 1,3-Dipolar Cycloaddition of Azomethine Ylides to Сyclopropenes

Synthesis ◽  
2018 ◽  
Vol 51 (03) ◽  
pp. 713-729 ◽  
Author(s):  
Vitali Boitsov ◽  
Alexander Stepakov ◽  
Alexander Filatov ◽  
Nickolay Knyazev ◽  
Stanislav Shmakov ◽  
...  
Keyword(s):  
Antitumor Activity ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Economic Method ◽  
Reaction Proceeds ◽  
High Yields

A simple, efficient and atom-economic method has been developed for the synthesis of complex alkaloid-like compounds with spiro-fused indolo[2,1-b]quinazoline and cyclopropa[a]pyrrolizine or 3-azabicyclo[3.1.0]hexane moieties. We have found that one-pot, three-component 1,3-dipolar cycloaddition reactions allow the desired products to be obtained from various cyclopropene derivatives with tryptanthrin-derived azomethine ylides generated in situ, in good to high yields and excellent diastereoselectivity. The possibility of ylide generation was exemplified by using α-amino acids (l-proline, l-4-thiazolidincarboxylic acid) and simplest peptides (dipeptide Gly-Gly, tripeptide Gly-Gly-Gly). Quantum chemical investigations indicate that the reaction proceeds through the S-shaped azomethine ylide, the interaction of which with cyclopropenes proceeds via a less sterically hindered endo-transition state. The antitumor activity of some of spiro-tryptanthrin derivatives against erythroleukemia (K562), cervical carcinoma (HeLa) and colon carcinoma (CT26) cell lines was evaluated in vitro by MTS-assay.

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.

scholarly journals Synthesis of pyrrolizidines and indolizidines by multicomponent 1,3-dipolar cycloaddition of azomethine ylides

2019 ◽  
Vol 91 (4) ◽  
pp. 575-596 ◽  
Author(s):  
Carmen Nájera ◽  
José Miguel Sansano
Keyword(s):  
Amino Acid ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
Amino Acid Derivatives ◽  
Reaction Conditions ◽  
Dipolar Cycloadditions ◽  
Spiro Derivatives ◽  
Stabilized Azomethine Ylides

Abstract Different multicomponent 1,3-dipolar cycloadditions (1,3-DC) of cyclic α-amino acid derivatives with aldehydes and dipolarophiles have been described as efficient and simple methodologies for the synthesis of the pyrrolidine unit of pyrrolizidines and indolizidines. When free cyclic α-amino acids are used, a thermal promoted decarboxylative process generates in situ the corresponding non-stabilized azomethine ylides, which afforded the corresponding pyrrolizidines and indolizidines with a hydrogen in the bicyclic units. This methodology has been employed to the synthesis of complex systems including spiro derivatives when ketones are used as carbonyl component. In addition, working with cyclic α-amino acid derived esters, the three-component 1,3-DC takes place under milder reaction conditions giving the corresponding pyrrolizidines and indolizidines with an alkoxycarbonyl group in the bridge adjacent carbon to the nitrogen. This methodology can be carried out by a double consecutive or stepwise 1,3-DC to provide pyrrolizidines via the precursor prolinates. The conformation of the azomethine ylide controls the endo/exo diastereoselectivity of the 1,3-DC.

scholarly journals Endo-Selective Construction of Spiro-[butyrolactone-pyrrolidine] via Ag(I)/CAAA-Amidphos-Catalyzed 1,3-Dipolar Cycloaddition between Azomethine Ylides and α-Methylene-γ-Butyrolactone

Catalysts ◽  
2019 ◽  
Vol 10 (1) ◽  
pp. 28 ◽  
Author(s):  
Qinglin Hou ◽  
Yaoyao You ◽  
Xinluo Song ◽  
Yingxia Wang ◽  
Ke Chen ◽  
...  
Keyword(s):  
Organic Chemistry ◽  
Catalytic System ◽  
Azomethine Ylides ◽  
Dipolar Cycloaddition ◽  
Effective Strategy ◽  
Optimal Conditions ◽  
One Pot ◽  
Synthetic Organic Chemistry ◽  
Quaternary Stereocenter

Construction of spirocyclic pyrrolidines bearing a spiro quaternary stereocenter is an enormous challenge in synthetic organic chemistry. In this report, we introduce a Ag(I)/CAAA-amidphos-catalyzed enantioselective 1,3-dipolar cycloaddition between azomethine ylides and α-methylene-γ-butyrolactone as an effective strategy for the construction of excellent endo-selective spiro-[butyrolactone-pyrrolidine] derivatives. Meanwhile, the catalytic system was also successfully applied in the three-component one-pot reaction of azomethine ylides formed in situ under the action of N,N′-diisopropylcarbodiimide serving as a dehydrator. Under the optimal conditions, endo-pyrrolidine derivatives bearing a spiro quaternary stereocenter were obtained with high to excellent yields (up to 95% yield) and enantioselectivities (up to 93% ee).

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.

Bioinspired Catalysis: Self-Assembly of a Protein and DNA as a Catalyst for the Aldol Reaction in Aqueous Media

Synlett ◽  
2017 ◽  
Vol 29 (05) ◽  
pp. 560-565 ◽  
Author(s):  
Guangxun Li ◽  
Zhuo Tang ◽  
Hongxin Liu ◽  
Ying-wei Wang ◽  
Shiqi Zhang
Keyword(s):  
Catalytic System ◽  
Electrostatic Interaction ◽  
Self Assembly ◽  
Aldol Reaction ◽  
Aqueous Media ◽  
Aldol Reactions ◽  
Mild Conditions ◽  
Self Assembling ◽  
High Yields

An interesting bioinspired catalyst formed from readily available DNA and a protein through electrostatic interaction in situ proved to be efficient in catalyzing aldol reactions under mild conditions in water. By using a self-assembling catalytic system formed from protamine and DNA, aldol adducts were obtained with high yields and moderate enantioselectivities. Preliminary experiments demonstrated that the chirality of the DNA could be effectively transferred to the reaction product through the bound molecules or proteins.

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