scholarly journals Cyclic cis-1,3-Diamines Derived from Bicyclic Hydrazines: Synthesis and Applications

Synlett ◽  
2020 ◽  
Author(s):  
Erica Benedetti ◽  
Laurent Micouin ◽  
Claire Fleurisson
Keyword(s):  
Bond Cleavage ◽  
Building Blocks ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Chemical Similarity ◽  
Active Compounds ◽  
General Overview ◽  
Biological Interest ◽  
Potential Applications ◽  
Rna Binders

AbstractCyclic cis-1,3-diamines are versatile building blocks frequently found in natural molecules or biologically active compounds. In comparison with widely studied 1,2-diamines, and despite their chemical similarity, 1,3-diamines have been investigated less intensively probably because of a lack of general synthetic procedures giving access to these compounds with good levels of chemo-, regio-, and stereocontrol. In this Account we will give a general overview of the biological interest of cyclic cis-1,3-diamines. We will then describe the synthesis and potential applications of these compounds with a particular focus on the work realized in our laboratory.1 Introduction2 Biological Relevance of the cis-1,3-Diamine Motif3 Classical Synthetic Strategies towards cis-1,3-Diamines4 N–N Bond Cleavage of Bicyclic Hydrazines: A Versatile Method to Access cis-1,3-Diamines4.1 Preparation of Five-Membered Cyclic cis-1,3-Diamino Alcohols4.2 Access to Fluorinated 1,3-cis-Diaminocyclopentanes4.3 Synthesis of cis-1,3-Diaminocyclohexitols4.4 Formation of Cyclic cis-3,5-Diaminopiperidines5 Applications of Cyclic cis-1,3-Diamines5.1 Small-Molecular RNA Binders5.2 Fluorinated 1,3-Diamino Cyclopentanes as NMR Probes6 Concluding Remarks

scholarly journals Organocatalytic atroposelective synthesis of axially chiral styrenes

2017 ◽  
Vol 8 (1) ◽  
Author(s):  
Sheng-Cai Zheng ◽  
San Wu ◽  
Qinghai Zhou ◽  
Lung Wa Chung ◽  
Liu Ye ◽  
...  
Keyword(s):  
Asymmetric Catalysis ◽  
Addition Reaction ◽  
Building Blocks ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Chiral Compounds ◽  
Axially Chiral ◽  
Potential Applications ◽  
Styrene Derivatives

Abstract Axially chiral compounds are widespread in biologically active compounds and are useful chiral ligands or organocatalysts in asymmetric catalysis. It is well-known that styrenes are one of the most abundant and principal feedstocks and thus represent excellent prospective building blocks for chemical synthesis. Driven by the development of atroposelective synthesis of axially chiral styrene derivatives, we discovered herein the asymmetric organocatalytic approach via direct Michael addition reaction of substituted diones/ketone esters/malononitrile to alkynals. The axially chiral styrene compounds were produced with good chemical yields, enantioselectivities and almost complete E/Z-selectivities through a secondary amine-catalysed iminium activation strategy under mild conditions. Such structural motifs are important precursors for further transformations into biologically active compounds and synthetic useful intermediates and may have potential applications in asymmetric synthesis as olefin ligands or organocatalysts.

Electrochemical Regioselective C–H Selenylation of 2H-Indazole Derivatives

2021 ◽  
Author(s):  
Zhixiong Ruan ◽  
Shengsheng Lin ◽  
Xiaomei Cheng ◽  
Hasimujiang Balati ◽  
Zhongnan Xu ◽  
...  
Keyword(s):  
Environmentally Friendly ◽  
Building Blocks ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds

The selenium-substituted heteroarenes are biologically active compounds and useful building blocks. In this sequence, we have developed a metal-and oxidant-free, environmentally friendly protocol for the regioselective selenylation of 2H-indazole derivatives...

Recent Advances in the Green Synthesis of Heterocycles: From Building Blocks to Biologically Active Compounds

2021 ◽  
Vol 18 ◽  
Author(s):  
Christian Schäfer ◽  
Hyejin Cho ◽  
Bernadett Vlocskó ◽  
Guoshu Xie ◽  
Béla Török
Keyword(s):  
Green Synthesis ◽  
Building Blocks ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Environmentally Benign ◽  
Active Compounds ◽  
Aromatic Heterocycles ◽  
High Interest ◽  
Recent Advances ◽  
Benign Synthesis

: Recent advances in the environmentally benign synthesis of common heterocycles are described. This account features three main parts; the preparation of non-aromatic heterocycles, one-ring aromatic heterocycles and their condensed analogs. Due to the great variety of and high interest in these compounds, this work focuses on providing representative examples of the preparation of the target compounds.

scholarly journals 1,3-Cyclohexadien-1-Als: Synthesis, Reactivity and Bioactivities

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1772
Author(s):  
Ignacio E. Tobal ◽  
Rocío Bautista ◽  
David Diez ◽  
Narciso M. Garrido ◽  
Pilar García-García
Keyword(s):  
Organic Chemistry ◽  
Building Block ◽  
Building Blocks ◽  
Natural Compounds ◽  
Diels Alder ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Complex Molecules ◽  
Active Compounds ◽  
Electron Withdrawing Group

In synthetic organic chemistry, there are very useful basic compounds known as building blocks. One of the main reactions wherein they are applied for the synthesis of complex molecules is the Diels–Alder cycloaddition. This reaction is between a diene and a dienophile. Among the most important dienes are the cyclic dienes, as they facilitate the reaction. This review considers the synthesis and reactivity of one of these dienes with special characteristics—it is cyclic and has an electron withdrawing group. This building block has been used for the synthesis of biologically active compounds and is present in natural compounds with interesting properties.

scholarly journals Application of the ring-closing metathesis to the formation of 2-aryl-1 H -pyrrole-3-carboxylates as building blocks for biologically active compounds

Tetrahedron ◽  
2016 ◽  
Vol 72 (47) ◽  
pp. 7462-7469 ◽  
Author(s):  
Katarzyna Grychowska ◽  
Bartłomiej Kubica ◽  
Marcin Drop ◽  
Evelina Colacino ◽  
Xavier Bantreil ◽  
...  
Keyword(s):  
Building Blocks ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Ring Closing Metathesis ◽  
Active Compounds

scholarly journals DABCO bond cleavage for the synthesis of piperazine derivatives

RSC Advances ◽  
2019 ◽  
Vol 9 (62) ◽  
pp. 36386-36409 ◽  
Author(s):  
Azim Ziyaei Halimehjani ◽  
Elham Badali
Keyword(s):  
Bond Cleavage ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Piperazine Derivatives

The applications of DABCO (1,4-diazabicyclo[2.2.2]octane) in the synthesis of piperazine derivatives including biologically active compounds via C–N bond cleavage are investigated in this review.

New processes for the synthesis of biologically relevant heterocycles

2008 ◽  
Vol 80 (4) ◽  
pp. 669-679 ◽  
Author(s):  
Martin G. Banwell
Keyword(s):  
Building Blocks ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Active Compounds ◽  
Biologically Relevant

This article describes the utility of certain readily accessible, ring-fused gem-dihalogenocyclopropanes as building blocks for the synthesis of heterocyclic and biologically active compounds.

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