scholarly journals Benzotriazol-1-yl-Acetone as a Building Block in Heterocyclic Chemistry: A Route to Benzotriazolylpyridazines, Benzotriazolylphthalazines and Benzotriazolylpyrazolo[5,1-c]-1,2,4-triazines

1999 ◽  
Vol 23 (11) ◽  
pp. 648-649
Author(s):  
Abdul Aziz Al-Naggar ◽  
Mervat Mohammed Abdel-Khalik ◽  
Mohammed Hilmy Elnagdi
Keyword(s):  
Double Bond ◽  
Building Block ◽  
Ethyl Cyanoacetate ◽  
Diazonium Salts ◽  
Heterocyclic Chemistry

Benzotriazolylacetone is coupled with aromatic diazonium salts to yield arylhydrazones, which can be condensed with ethyl cyanoacetate yielding pyridazinones whose reactivity towards activated double bond systems is investigated.

scholarly journals Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks

2013 ◽  
Vol 9 ◽  
pp. 2395-2403 ◽  
Author(s):  
Felix Wojcik ◽  
Sinaida Lel ◽  
Alexander G O’Brien ◽  
Peter H Seeberger ◽  
Laura Hartmann
Keyword(s):  
Double Bond ◽  
Building Block ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Building Blocks ◽  
Phase Synthesis ◽  
Highly Efficient ◽  
Monomer Sequence ◽  
Full Control ◽  
Block Approach

We present the solid phase synthesis of carbohydrate-functionalized oligo(amidoamines) with different functionalization patterns utilizing a novel alphabet of six differently glycosylated building blocks. Highly efficient in flow conjugation of thioglycosides to a double-bond presenting diethylentriamine precursor is the key step to prepare these building blocks suitable for fully automated solid-phase synthesis. Introduction of the sugar ligands via functionalized building blocks rather than postfunctionalization of the oligomeric backbone allows for the straightforward synthesis of multivalent glycoligands with full control over monomer sequence and functionalization pattern. We demonstrate the potential of this building-block approach by synthesizing oligomers with different numbers and spacing of carbohydrates and also show the feasibility of heteromultivalent glycosylation patterns by combining building blocks presenting different mono- and disaccharides.

Bicyclopropylidene. A unique tetrasubstituted alkene and versatile C6-building block for organic synthesis

2000 ◽  
Vol 72 (9) ◽  
pp. 1745-1756 ◽  
Author(s):  
Gary A. Molander
Keyword(s):  
Double Bond ◽  
Organic Synthesis ◽  
Building Block ◽  
Aryl Halides ◽  
Polymer Support ◽  
Additional Dimension ◽  
Palladium Catalyzed ◽  
Cleavage Step ◽  
Combinatorial Sense ◽  
Single Bonds

Bicyclopropylidene (4), now readily available in preparatively viable quantities, is evolving as a useful C6 building block for organic synthesis due to its enhanced reactivity at the C-H, the C=C, as well as both types of C-C single bonds. Monosubstituted derivatives are accessible by deprotonation/electrophilic substitution. Di- and tetrasubstituted bicyclopropylidenes are best made by copper-mediated reductive dimerization of bromolithiocarbenoids. The 1,3-dipolar cycloadducts of nitrones rearrange to spirocyclopropanated piperidones, palladium-catalyzed codimerizations with acrylates occur with opening of one of the rings to yield precursors to bicyclo[3.3.0]octene and bicyclo[5.3.0]decene skeletons. Silicon-heteroatom bonds can be added across the double bond of 4 under palladium catalysisjust like across a C텡C triple bond, and carbopalladation of the double bond in 4 occurs more rapidly than that in an acrylate. A variety of new three-component reactions of 4 with alkenyl as well as aryl halides and dienophiles have been developed and extended to be carried out in a combinatorial sense, even on a polymer support, with an additional dimension added in the cleavage step. Most of the reported reactions of bicyclopropylidene (4) proceed with good to excellent yields.

1-(Trimethylsilyl)vinyl MIDA Boronate: A Trifunctional C2 Building Block

Synthesis ◽  
2018 ◽  
Vol 50 (09) ◽  
pp. 1857-1861 ◽  
Author(s):  
Oleksandr Grygorenko ◽  
Yevhen Ivon ◽  
Zoya Voitenko
Keyword(s):  
Double Bond ◽  
Building Block ◽  
Title Compound ◽  
Vinyl Silane

1-(Trimethylsilyl)vinyl MIDA boronate — a trifunctional C2 building block — is prepared in only two laboratory steps and 54% overall yield starting from readily available trimethyl(vinyl)silane. The title compound undergoes orthogonal functionalization at either of the groups present in its structure, for example, iodination at the trimethylsilyl moiety, epoxidation at the double bond, and Suzuki–Miyaura coupling at the MIDA boronate.

scholarly journals Core and Double Bond Functionalization of Cyclopentadithiophene- Phosphaalkenes

2020 ◽  
Author(s):  
Jordann A.L. Wells ◽  
Muhammad Anwar Shameem ◽  
Arvind Kumar Gupta ◽  
Andreas Orthaber
Keyword(s):  
Double Bond ◽  
Solid State ◽  
Electronic Properties ◽  
Building Block ◽  
Metal Coordination ◽  
Bond Functionalization ◽  
Electronic Tuning ◽  
Optical And Electronic Properties ◽  
Donor And Acceptor ◽  
Solid State Structures

The heterofulvenoid cyclopentadithiophene-phosphaalkene is a versatilie building block for opto-electronic tuning with donor and acceptor moieties. Both the annulated thienyl rings and the phosphaalkene bond can be functionalised using a variety of chemical transfomations, e.g. forming C-C, C-E (E = Si, Br) bonds or oxidation and metal coordination, respectively. Solid-state structures, optical and electronic properties are probed theoretically and experimentally, illustrating the opto-electronic tailoring opportunities at this motif.

scholarly journals Ferulic Acid as Building Block for the Lipase-Catalyzed Synthesis of Biobased Aromatic Polyesters

Polymers ◽  
2021 ◽  
Vol 13 (21) ◽  
pp. 3693
Author(s):  
Alfred Bazin ◽  
Luc Avérous ◽  
Eric Pollet
Keyword(s):  
Double Bond ◽  
Thermal Resistance ◽  
Ferulic Acid ◽  
Building Block ◽  
Enzymatic Synthesis ◽  
Enzymatic Catalysis ◽  
Research Field ◽  
First Time ◽  
Aromatic Polyesters ◽  
Catalyzed Polymerization

Enzymatic synthesis of aromatic biobased polyesters is a recent and rapidly expanding research field. However, the direct lipase-catalyzed synthesis of polyesters from ferulic acid has not yet been reported. In this work, various ferulic-based monomers were considered for their capability to undergo CALB-catalyzed polymerization. After conversion into diesters of different lengths, the CALB-catalyzed polymerization of these monomers with 1,4-butanediol resulted in short oligomers with a DPn up to 5. Hydrogenation of the double bond resulted in monomers allowing obtaining polyesters of higher molar masses with DPn up to 58 and Mw up to 33,100 g·mol−1. These polyesters presented good thermal resistance up to 350 °C and Tg up to 7 °C. Reduction of the ferulic-based diesters into diols allowed preserving the double bond and synthesizing polyesters with a DPn up to 19 and Mw up to 15,500 g·mol−1 and higher Tg (up to 21 °C). Thus, this study has shown that the monomer hydrogenation strategy proved to be the most promising route to achieve ferulic-based polyester chains of high DPn. This study also demonstrates for the first time that ferulic-based diols allow the synthesis of high Tg polyesters. Therefore, this is an important first step toward the synthesis of competitive biobased aromatic polyesters by enzymatic catalysis.

scholarly journals Synthesis and Anticancer Perspective of Pyridopyrimidine Scaffold - An Overview

2021 ◽  
pp. 438-461
Author(s):  
Chaithra R. Shetty ◽  
C. S. Shastry
Keyword(s):  
Carboxylic Acid ◽  
Anticancer Activity ◽  
Building Block ◽  
Heterocyclic Chemistry ◽  
Active Compounds ◽  
Pyridine Carboxylic Acid ◽  
Anticancer Properties ◽  
The Core ◽  
Wide Range ◽  
Pyridine Carboxylic

The core pyridopyrimidines are gaining interest in organic and heterocyclic chemistry in recent days, as this scaffold acts as a building block because of its wide range of biological and pharmacological applications like anticancer, antimicrobial, fungicidal, antiviral, CNS, antibacterial, and anti-inflammatory properties. This review mainly emphasizes the evolution in anticancer properties of pyridopyrimidines since 2008 especially the method of synthesis and anticancer activity of synthesized compounds with reporting of active anticancer scaffolds. Important starting materials which are widely used for the synthesis are 2-thioxopyrimidine, ethyl 2-cyanoacetate, 2-amino-3-cyano-4-trifluoromethyl-6-phenyl-pyridine, 2-amino-4,6-disubstituted nicotinonitrile, 2-chloro-3-pyridine carboxylic acid, in which 2-thioxopyrimidine is found to be mostly employed in the synthesis. Pyridopyrimidines which are synthesized from different starting materials, in which the more active compounds are reported here which may help in further discovery/ development of novel molecules.

Alkyl Heteroaromatics as Building Blocks in Organic Synthesis: The Reactivity of Alkyl Azoles toward Electrophilic Reagents

1999 ◽  
Vol 54 (7) ◽  
pp. 923-928 ◽  
Author(s):  
I. S. Abdel Hafiz ◽  
A. A. Hassanien ◽  
A. M. Hussein
Keyword(s):  
Acetic Anhydride ◽  
Organic Synthesis ◽  
Ethyl Cyanoacetate ◽  
Aromatic Aldehydes ◽  
Building Blocks ◽  
Subsequent Treatment ◽  
Diazonium Salts ◽  
Phenyl Hydrazine ◽  
Electrophilic Reagents

Oxazolone (1) couples with aromatic diazonium salts to yield the arylhydrazones (3a-c). Compound 3 reacts with aniline to give aryl hydrazone (5). Compound 5 was also obtained via converting 1 into the imidazolone (4) and subsequent treatment of 4 with aromatic diazonium salts. Compounds 1 and 12 reacted with arylidenemalononitrile (6) to yield compounds 8 and 14 respectively. Also compounds 1, 12 condensed with an aromatic aldehydes to yield 11 and 17. Compounds 11, 17 reacted further with one molecule of malononitrile to give compounds 8 and 14, respectively. Compound 20 which was generated in situ by heating phenacylthiocyanate (19) in acetic anhydride on treatment with hydrazine hydrate or phenyl hydrazine gives 21 and 22 respectively. A lso 20 reacted with malononitrile or with ethyl cyanoacetate to give 23 and 24, respectively.

scholarly journals Core and Double Bond Functionalization of Cyclopentadithiophene- Phosphaalkenes

2020 ◽  
Author(s):  
Jordann A.L. Wells ◽  
Muhammad Anwar Shameem ◽  
Arvind Kumar Gupta ◽  
Andreas Orthaber
Keyword(s):  
Double Bond ◽  
Solid State ◽  
Electronic Properties ◽  
Building Block ◽  
Metal Coordination ◽  
Bond Functionalization ◽  
Electronic Tuning ◽  
Optical And Electronic Properties ◽  
Donor And Acceptor ◽  
Solid State Structures

The heterofulvenoid cyclopentadithiophene-phosphaalkene is a versatilie building block for opto-electronic tuning with donor and acceptor moieties. Both the annulated thienyl rings and the phosphaalkene bond can be functionalised using a variety of chemical transfomations, e.g. forming C-C, C-E (E = Si, Br) bonds or oxidation and metal coordination, respectively. Solid-state structures, optical and electronic properties are probed theoretically and experimentally, illustrating the opto-electronic tailoring opportunities at this motif.

Zur Reaktivität von C=N-Doppelbindungssystemen, VII. Synthesen von fluoreszierenden pyronokondensierten Heterocyclen / The Reactivity of the C=N-Double Bond Systems, VII. Syntheses of Condensed Pyronoheterocycles

1976 ◽  
Vol 31 (4) ◽  
pp. 514-519 ◽  
Author(s):  
Otto S. Wolfbeis ◽  
Erich Ziegler
Keyword(s):  
Double Bond ◽  
Ethyl Cyanoacetate ◽  
Hydroxy Coumarin ◽  
Combined Action

The combined action of orthoformate and aniline upon 4-hydroxy-coumarin yields anilinomethylene chromon-2,4-dione, which reacts with ethyl cyanoacetate in DMF in the presence of KOH to give the pyronocoumarine (6a). Pyronoquinolones are obtained in a similar way.

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