A catalyst-free 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines and 3-nitroindoles: an easy access to five-ring-fused tetrahydroisoquinolines

A concise, atom-economic, and highly regioselective synthetic strategy for the construction of several dinitrogen-fused heterocycles bearing bisphosphonates by 1,3-dipolar cycloaddition reaction of azomethine imines with tetraethyl vinylidene-1,1-bisphosphonate in the presence of CuI in toluene media has been developed. The targeted compounds were obtained in good yields and with excellent regioselectivity. This method for the synthesis of gem-bisphosphonates (BPs) is particularly attractive due to features such as low cost, mild conditions, atom economy, high stereoselectivity, and potential biological activity of the product.

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Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones

Molecules ◽

10.3390/molecules26102969 ◽

2021 ◽

Vol 26 (10) ◽

pp. 2969

Author(s):

Guipeng Feng ◽

Guoyang Ma ◽

Wenyan Chen ◽

Shaohong Xu ◽

Kaikai Wang ◽

...

Keyword(s):

Asymmetric Synthesis ◽

Functional Groups ◽

Absolute Configuration ◽

Dipolar Cycloaddition ◽

Quantum Electronic ◽

Mild Conditions ◽

Spectrum Method ◽

Wide Range ◽

Reaction Proceeds ◽

Azomethine Imines

[3 + 2] A 1,3-Dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. An array of tetrahydroisoquinoline derivatives is generally constructed with good diastereoselectivities and enantioselectivities (up to >25:1 dr, >95% ee). Moreover, the absolute configuration of the product was previously determined by using the quantum electronic circular dichroism calculation and ECD spectrum method.

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Catalyst-free Synthesis of Spiro[indoline-3,1′-pyrazolo[5,1-a]isoquinolines]viaDiastereoselective 1,3-dipolar Cycloaddition under Mild Conditions

Journal of Heterocyclic Chemistry ◽

10.1002/jhet.2903 ◽

2017 ◽

Vol 54 (5) ◽

pp. 2922-2928 ◽

Cited By ~ 6

Author(s):

Fangzhi Hu ◽

Hui Chen ◽

Minmin Zhang ◽

Shuowen Yu ◽

Xiaoying Xu ◽

...

Keyword(s):

Dipolar Cycloaddition ◽

Mild Conditions ◽

Catalyst Free

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Catalyst-free and atom-economical 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines: Facile synthesis of isoquinoline-fused spirocycles

Green Synthesis and Catalysis ◽

10.1016/j.gresc.2021.11.005 ◽

2021 ◽

Author(s):

Lesong Li ◽

Tao Liu ◽

Xiaoli Zhang ◽

Xiaohan Hou ◽

Hao Dong ◽

...

Keyword(s):

Dipolar Cycloaddition ◽

Facile Synthesis ◽

Catalyst Free ◽

Azomethine Imines

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ChemInform Abstract: Catalyst-Free 1,3-Dipolar Cycloaddition: An Efficient Route for the Formation of the 1,2,3-Triazole-Fused Diazepinone Framework.

ChemInform ◽

10.1002/chin.201028177 ◽

2010 ◽

Vol 41 (28) ◽

pp. no-no

Author(s):

K. C. Majumdar ◽

Krishanu Ray ◽

Sintu Ganai ◽

Tapas Ghosh

Keyword(s):

Dipolar Cycloaddition ◽

Catalyst Free ◽

Efficient Route

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Continuous flow processes for the S-alkynylation of cysteine-containing peptides and thioglycoside under catalyst-free, oxidant-free and mild conditions

Green Chemistry ◽

10.1039/d1gc01937f ◽

2021 ◽

Author(s):

Long-Zhou Qin ◽

Xin Yuan ◽

Jie Liu ◽

Meng-yu Wu ◽

Qi Sun ◽

...

Keyword(s):

Continuous Flow ◽

Mild Conditions ◽

Catalyst Free ◽

Flow Processes ◽

Novel Method

Herein, we develop a novel method for the selective alkynylation of cysteine-containing peptides and 1-thioglycoside residues by the use of continuous flow. This method was characterised by the mild conditions...

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