scholarly journals Programmed Sequential Additions to Halogenated Mucononitriles

2020 ◽  
Author(s):  
Adam Zahara ◽  
Elsa Hinds ◽  
Andrew Nguyen ◽  
Sidney Wilkerson-Hill
Keyword(s):  
Natural Product ◽  
Intramolecular Cyclization ◽  
Conjugate Addition ◽  
Secondary Amines ◽  
Addition Reactions ◽  
Cyclization Reactions ◽  
Carbon Nucleophiles ◽  
Multicomponent Coupling

Dihalomucononitriles were synthesized and their reactivity evaluated to assess their ability to function as linchpin reagents. Bis(2-chloroacrylonitrile) and bis(2-bromoacrylonitrile) were synthesized from 2,13-benzothiadiazole and shown to undergo conjugate addition reactions with both nitrogen (40–95% yield) and carbon nucleophiles (72–93% yield). Secondary amines were found to undergo monoadditions while carbon nucleophiles added twice. The sequence of addition of the nucleophiles could be controlled giving mixed addition products. The multicomponent coupling products could then be converted to natural product-like motifs using intramolecular cyclization reactions.

scholarly journals Programmed Sequential Additions to Halogenated Mucononitriles

2020 ◽  
Author(s):  
Adam Zahara ◽  
Elsa Hinds ◽  
Andrew Nguyen ◽  
Sidney Wilkerson-Hill
Keyword(s):  
Natural Product ◽  
Intramolecular Cyclization ◽  
Conjugate Addition ◽  
Secondary Amines ◽  
Addition Reactions ◽  
Cyclization Reactions ◽  
Carbon Nucleophiles ◽  
Multicomponent Coupling

Dihalomucononitriles were synthesized and their reactivity evaluated to assess their ability to function as linchpin reagents. Bis(2-chloroacrylonitrile) and bis(2-bromoacrylonitrile) were synthesized from 2,13-benzothiadiazole and shown to undergo conjugate addition reactions with both nitrogen (40–95% yield) and carbon nucleophiles (72–93% yield). Secondary amines were found to undergo monoadditions while carbon nucleophiles added twice. The sequence of addition of the nucleophiles could be controlled giving mixed addition products. The multicomponent coupling products could then be converted to natural product-like motifs using intramolecular cyclization reactions.

ChemInform Abstract: Conjugate Addition Reactions of Carbon Nucleophiles to Electron-Deficient Dienes.

ChemInform ◽  
2011 ◽  
Vol 42 (7) ◽  
pp. no-no
Author(s):  
Aurelio G. Csaky ◽  
Gabriela de la Herran ◽  
M. Carmen Murcia
Keyword(s):  
Conjugate Addition ◽  
Addition Reactions ◽  
Carbon Nucleophiles ◽  
Electron Deficient Dienes

Synthesis and Analysis of Natural‐Product‐Like Macrocycles by Tandem Oxidation/Oxa‐Conjugate Addition Reactions

2019 ◽  
Vol 25 (26) ◽  
pp. 6500-6504 ◽  
Author(s):  
Hyunji Lee ◽  
Kayla Sylvester ◽  
Emily R. Derbyshire ◽  
Jiyong Hong
Keyword(s):  
Natural Product ◽  
Conjugate Addition ◽  
Addition Reactions

New Preparation of 2-N-Alkyl(aryl)amino-5-methyl-4H-1,3-thiazin-4-ones and 3,4-Dihydro-5-methyl-2,4-dioxo-2H-1,3-thiazine

1993 ◽  
Vol 58 (4) ◽  
pp. 893-901 ◽  
Author(s):  
Dušan Koščík ◽  
Milan Dzurilla ◽  
Peter Kutschy
Keyword(s):  
Mass Spectroscopy ◽  
Secondary Amines ◽  
Addition Reactions ◽  
Cyclization Reactions ◽  
Alkyl Aryl ◽  
New Approach ◽  
H Nmr ◽  
Primary And Secondary Amines ◽  
Sole Product ◽  
C Nmr

Addition-cyclization reactions of 3-bromo- and 3-chloro-2-methylpropenoylisothiocyanates with primary and secondary amines and alcohols have been studied. The formed addition products, thioureas, underwent cyclization of heating with ethanolic KOH or in dimethylformamide in the presence of lithium hydride. This method represents a new approach to 2-dialkyl(aryl)amino-5-methyl-4H-1,3-thiazin-4-ones. Addition reactions with alcohols afforded 3,4-dihydro-5-methyl-2,4-dioxo-2H-1,3-thiazine as the sole product. The structure of the synthesized compounds was confirmed by 1H NMR, 13C NMR, IR and mass spectroscopy.

Stereoselective Preparation of Bicyclo[3.3.0]octanones From the Products of Aprotic Conjugate Addition of Lithiated Allylic Sulfoxides to Cyclopent-2-enone and Enolate Trapping With Methyl Cyanoformate

1989 ◽  
Vol 42 (9) ◽  
pp. 1455 ◽  
Author(s):  
RK Haynes ◽  
AG Katsifis
Keyword(s):  
Intramolecular Cyclization ◽  
Phosphine Oxide ◽  
Conjugate Addition ◽  
Cyclization Reactions ◽  
Lithium Enolates

The lithium enolates arising by aprotic conjugate addition of lithiated but-2-enyl sulfoxides and a phosphine oxide to cyclopent-2-enone react efficiently with methyl cyanoformate to give the corresponding methyl 5-oxocyclopentanecarboxylates in good yields. The sulfoxides are smoothly deoxygenated with tributylphosphine diiodide in ether at 0�, and the resulting sulfides undergo intramolecular cyclization in the presence of tin(IV)chloride to give methyl oxobicyclo [3.3.0] octanecarboxylates , again in good to excellent yields. The cyclizations are highly stereoselective in that the syn- and anti-stereochemistries of the enolate trapped products obtained from (E)-and (Z)- sulfoxides are quantitatively reflected in the products obtained from the cyclization reactions.

Access to pyrrole-based heterocyclic compounds via addition of pyrrole to C=C and C=N bonds

2014 ◽  
Vol 86 (6) ◽  
pp. 925-932 ◽  
Author(s):  
Canan Unaleroglu ◽  
Baris Temelli ◽  
Dilek Isik Tasgin
Keyword(s):  
Intramolecular Cyclization ◽  
Heterocyclic Compounds ◽  
The Other ◽  
Addition Reactions ◽  
Cyclization Reactions ◽  
Reaction Conditions ◽  
Unsaturated Compounds ◽  
Intermolecular Cyclization

AbstractA series of metal triflate-catalyzed addition reactions of pyrrole to C=C and C=N bonds have been investigated to access pyrrole-based heterocyclic compounds. The addition of pyrrole to different α,β-unsaturated compounds or N-tosyl imines afforded suitable structures for the construction of [5-5] bicyclic systems or porphyrins, respectively. Intramolecular cyclization reactions were applied for the synthesis of pyrrolizine derivatives. In the other reaction mode, intermolecular cyclization reactions gave A4- and trans-A2B2-meso-substituted porphyrins under mild reaction conditions with low scrambling.

Exploring bis-(amino)cyclopropenylidene as a non-covalent Brønsted base catalyst in conjugate addition reactions

2018 ◽  
Vol 16 (3) ◽  
pp. 384-388 ◽  
Author(s):  
Gurdeep Singh ◽  
Prithwish Goswami ◽  
Ramasamy Vijaya Anand
Keyword(s):  
Conjugate Addition ◽  
Addition Reactions ◽  
Base Catalyst ◽  
Quinone Methides ◽  
Carbon Nucleophiles ◽  
Catalytic Application ◽  
Brønsted Base

The catalytic application of bis-(amino)cyclopropenylidene, as a non-covalent Brønsted base, in the 1,4- and 1,6-conjugate addition of carbon nucleophiles to enones andp-quinone methides, respectively, is described.

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