The Sonogashira coupling of 2- and 4-ethynyl derivatives of proton sponge with 1,8-diiodonaphthalene: Novel cascade transformations into naphtho[1,2-k]fluoranthenes and acenaphtho[1,2-b]benzo[g]indoles

Tetrahedron ◽  
2018 ◽  
Vol 74 (1) ◽  
pp. 165-173
Author(s):  
Ekaterina A. Filatova ◽  
Anna V. Gulevskaya ◽  
Alexander F. Pozharskii ◽  
Vitaliy V. Suslonov
Keyword(s):  
Sonogashira Coupling ◽  
Proton Sponge ◽  
Derivatives Of

New 2-Alkynyl Derivatives of the Acyclic Nucleoside 9-(2,3-Dihydroxypropyl)adenine and Their 6-Guanidinopurine Counterparts as Potential Effectors of Adenosine Receptors

2003 ◽  
Vol 68 (11) ◽  
pp. 2201-2218 ◽  
Author(s):  
Michal Česnek ◽  
Antonín Holý ◽  
Milena Masojídková
Keyword(s):  
Adenosine Receptors ◽  
Sonogashira Coupling ◽  
Acyclic Nucleoside ◽  
Derivatives Of

A series of the new 2-alkynyl derivatives of the acyclic nucleoside 9-(2,3-dihydroxypropyl)- adenine and their 6-guanidinopurine analogues were prepared by the Sonogashira coupling. The effect of the prepared compounds on A1 and A2A receptors was examined.

scholarly journals Branching out at C-2 of septanosides. Synthesis of 2-deoxy-2-C-alkyl/aryl septanosides from a bromo-oxepine

2012 ◽  
Vol 8 ◽  
pp. 522-527 ◽  
Author(s):  
Supriya Dey ◽  
Narayanaswamy Jayaraman
Keyword(s):  
Suzuki Reaction ◽  
Ring Expansion ◽  
Protecting Groups ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Alkyl Aryl ◽  
Organometallic Reactions ◽  
Bond Forming ◽  
Derivatives Of ◽  
Cyclopropane Derivatives

This paper deals with the synthesis of 2-deoxy-2-C-alkyl/aryl septanosides. A range of such septanoside derivatives was synthesized by using a common bromo-oxepine intermediate, involving C–C bond forming organometallic reactions. Unsaturated, seven-membered septanoside vinyl bromides or bromo-oxepines, obtained through a ring expansion methodology of the cyclopropane derivatives of oxyglycals, displayed a good reactivity towards several acceptor moieties in C–C bond forming Heck, Suzuki and Sonogashira coupling reactions, thus affording 2-deoxy-2-C-alkyl/aryl septanosides. Whereas Heck and Sonogashira coupling reactions afforded 2-deoxy-2-C-alkenyl and -alkynyl derivatives, respectively, the Suzuki reaction afforded 2-deoxy-2-C-aryl septanosides. Deprotection and reduction of the 2-deoxy-2-alkenyl derivative afforded the corresponding 2-deoxy-2-C-alkyl septanoside free of protecting groups. The present study illustrates the reactivity of bromo-oxepine in the synthesis of hitherto unknown septanosides, branching out at C-2, through C–C bond formation with alkyl and aryl substituents.

10-Dimethylamino Derivatives of Benzo[h]quinoline and Benzo[h]quinazolines: Fluorescent Proton Sponge Analogues with Opposed peri-NMe2/–N═ Groups. How to Distinguish between Proton Sponges and Pseudo-Proton Sponges

2016 ◽  
Vol 81 (13) ◽  
pp. 5574-5587 ◽  
Author(s):  
Alexander F. Pozharskii ◽  
Valery A. Ozeryanskii ◽  
Vladimir Y. Mikshiev ◽  
Alexander S. Antonov ◽  
Anatoly V. Chernyshev ◽  
...  
Keyword(s):  
Proton Sponge ◽  
Proton Sponges ◽  
Derivatives Of

scholarly journals Structure of new derivatives of 1,8-diaminonaphthalenes ('proton sponge')

2006 ◽  
Vol 62 (a1) ◽  
pp. s294-s294
Author(s):  
O. Dyachenko ◽  
O. Kazheva ◽  
A. Pozharskii ◽  
V. Ozeryanskii
Keyword(s):  
Proton Sponge ◽  
Derivatives Of

Metal Complexes of Biologically Important Ligands, CLV [1]. Some Derivatives of 4-Ethynylphenylalanine

2004 ◽  
Vol 59 (8) ◽  
pp. 865-868 ◽  
Author(s):  
Armin Enzmann ◽  
Wolfgang Beck
Keyword(s):  
Methyl Ester ◽  
Metal Complexes ◽  
Sonogashira Coupling ◽  
Phenylalanine Methyl Ester ◽  
Derivatives Of

AbstractThe benzoyl protected 4-ethynyl-L-phenylalanine methyl ester gives with octacarbonyldicobalt and ethylene-bis(triphenylphosphine)platinum(0) the complexes Co2(CO)6(HC≡CR) and (Ph3P)2 Pt(HC≡CR) (R = p-C6H4CH2CH(CO2Me)N(HCOPh). The heterocumulene [Cp(Ph3P)2Ru=C=C(H)R]+BF4− (R = p-C6H4CH2C(H)N(H)-Boc is formed from [Cp(Ph3P)2Ru]+BF4− and N-t-Boc-4-ethynylphenylalanine methyl ester. The alkynyl bridged tetraamino acid with a tetraphenylmethane backbone C[p-C6H4C≡C-p-C6H4-CH2CH(CO2Me)NH-t- Boc]4 was synthesized from tetrakis(4-iodophenyl)methane and N-Boc-4-ethynylphenylalanine methyl ester by Sonogashira coupling.

ChemInform Abstract: Unexpected Formation of Diels-Alder Spiro Adducts from 4-Hydroxymethyl Derivatives of ′Proton Sponge′.

ChemInform ◽  
2010 ◽  
Vol 22 (35) ◽  
pp. no-no
Author(s):  
N. V. VISTOROBSKII ◽  
A. F. POZHARSKII ◽  
S. V. SHORSHNEV ◽  
A. I. CHERNYSHEV
Keyword(s):  
Diels Alder ◽  
Proton Sponge ◽  
Unexpected Formation ◽  
Derivatives Of

A new family of 1,4-diaryl-1,3-butadiynes based on the “proton sponge”: synthesis, electronic and chemical properties

2022 ◽  
Author(s):  
Ekaterina A. Filatova ◽  
Semyon V. Tsybulin ◽  
Dmitry A. Rybin ◽  
Valery A. Ozeryanskii ◽  
Anna V. Gulevskaya ◽  
...  
Keyword(s):  
Chemical Properties ◽  
Proton Sponge ◽  
New Family ◽  
Derivatives Of ◽  
And Chemical Properties

A new family of 1,4-diaryl-1,3-butadiynes containing two and four fragments of 1,8-bis(dimethylamino)naphthalene (DMAN or “proton sponge”) was synthesized using various 2- and 4-ethynyl derivatives of the proton sponge as synthetic...

The Synthesis of 10-Halo-Substituted Derivatives of nido-7,8,9-PC2B8H11 and [nido-7,8,9-PC2B8H10]- and New Linear Correlations Between NMR Parameters

2005 ◽  
Vol 70 (11) ◽  
pp. 1861-1872 ◽  
Author(s):  
Josef Holub ◽  
Mario Bakardjiev ◽  
Bohumil Štíbr
Keyword(s):  
Nmr Spectroscopy ◽  
Chemical Shifts ◽  
Proton Sponge ◽  
Nmr Chemical Shifts ◽  
Nmr Parameters ◽  
Neutral Compounds ◽  
Experimental Errors ◽  
Derivatives Of ◽  
Linear Correlations ◽  
Individual Cluster

Halogenation of the eleven-vertex phosphadicarbaborane nido-7,8,9-PC2B8H10 (1) with CCl4, Br2 or I2 in the presence of anhydrous AlCl3 (solvents CCl4, CS2, and benzene, respectively) generated a series of 10-X-nido-7,8,9-PC2B8H10 (10-X-1) compounds (X = Cl, Br, and I) in yields 55, 65, and 63%, respectively. Anionic compounds [10-X-nido-7,8,9-PC2B8H10]- (10-X-2) (X = Cl, Br, I) were obtained by treatment of the corresponding neutral compounds with "proton sponge" (PS = 1,8-bis(dimethylamino)naphthalene). All compounds were characterized by multinuclear (11B, 1H, and 31P) NMR spectroscopy and [11B-11B]-COSY and 1H-{11B(selective)} NMR measurements that led to complete assignments of all 11B and 1H resonances to individual cluster positions. Interesting halo-substitution NMR effects are also discussed in terms of new linear correlations. All the changes in NMR chemical shifts (∆) induced at the various skeletal sites by halogeno substituents on specific sites can be related to an arbitrary reference skeleton and are, within experimental errors, linearly proportional to those induced at the substituted site (∆α) of the reference skeleton.

Unexpected Formation of Diels–Alder Spiro Adducts from 4-Hydroxymethyl Derivatives of ‘Proton Sponge’

1991 ◽  
Vol 1 (1) ◽  
pp. 10-12 ◽  
Author(s):  
Nikolai V. Vistorobskii ◽  
Alexander F. Pozharskii ◽  
Sergei V. Shorshnev ◽  
Alexei I. Chernyshev
Keyword(s):  
Diels Alder ◽  
Proton Sponge ◽  
Unexpected Formation ◽  
Derivatives Of
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