Synthesis of spiro[2.5]octa-4,7-dien-6-one with consecutive quaternary centers via 1,6-conjugate addition induced dearomatization of para-quinone methides

2015 ◽  
Vol 51 (87) ◽  
pp. 15831-15834 ◽  
Author(s):  
Kuo Gai ◽  
Xinxin Fang ◽  
Xuanyi Li ◽  
Jinyi Xu ◽  
Xiaoming Wu ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Quinone Methides ◽  
One Pot ◽  
Quaternary Centers

Spiro[2.5]octa-4,7-dien-6-one with consecutive quaternary centers was synthesized in one pot without the use of metals.

1,6-Conjugate addition initiated formal [4+2] annulation of p-quinone methides with sulfonyl allenols: a unique access to spiro[5.5]undeca-1,4-dien-3-one scaffolds

2020 ◽  
Vol 56 (37) ◽  
pp. 5022-5025 ◽  
Author(s):  
Ganesh S. Ghotekar ◽  
Sachin R. Shirsath ◽  
Aslam C. Shaikh ◽  
M. Muthukrishnan
Keyword(s):  
Conjugate Addition ◽  
Quinone Methides ◽  
One Pot ◽  
One Pot Synthesis

An expedient one-pot synthesis of carbocyclic spiro[5.5]undeca-1,4-dien-3-ones via 1,6-conjugate addition initiated formal [4+2] annulation sequences by employing p-quinone methides and sulfonyl allenols.

scholarly journals One-pot synthesis of indoles and quinolinones from ortho-tosylaminophenyl-substituted para-quinone methides

RSC Advances ◽  
2020 ◽  
Vol 10 (55) ◽  
pp. 33455-33460
Author(s):  
Junwei Wang ◽  
Xiang Pan ◽  
Quanjin Rong ◽  
Lei Zhao ◽  
Lin Zhao ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Quinone Methides ◽  
One Pot ◽  
One Pot Synthesis

A facile one-pot synthesis has been developed through alkylation/acylation of ortho-tosylaminophenyl-substituted para-quinone methides followed by an intramolecular 1,6-conjugate addition and oxidation sequence.

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor-Acceptor Complex

2020 ◽  
Author(s):  
José Tiago Menezes Correia ◽  
Gustavo Piva da Silva ◽  
Camila Menezes Kisukuri ◽  
Elias André ◽  
Bruno Pires ◽  
...  
Keyword(s):  
Electron Donor ◽  
Functional Group ◽  
Photoexcited Electron ◽  
One Pot ◽  
Quaternary Centers ◽  
Metal Free ◽  
Acceptor Complex ◽  
Catalyst Free ◽  
Donor Acceptor ◽  
Radical Cascade

A metal- and catalyst-free photoinduced radical cascade hydroalkylation of 1,7-enynes has been disclosed. The process is triggered by a SET event involving a photoexcited electron-donor-aceptor complex between NHPI ester and Hantzsch ester, which decomposes to afford a tertiary radical that is readily trapped by the enyne. <a>The method provides an operationally simple, robust and step-economical approach to the construction of diversely functionalized dihydroquinolinones bearing quaternary-centers. A sequential one-pot hydroalkylation-isomerization approach is also allowed giving access to a family of quinolinones. A wide substrate scope and high functional group tolerance was observed in both approaches</a>.

Synthesis of Nitrile-Bearing Quaternary Centers via an Equilibrium-Driven Transnitrilation and Anion-Relay Strategy

2019 ◽  
Author(s):  
Sebastien Alazet ◽  
Michael West ◽  
Purvish Patel ◽  
Sophie Rousseaux
Keyword(s):  
Building Blocks ◽  
One Pot ◽  
Quaternary Centers ◽  
Synthetic Intermediates

The efficient preparation of nitrile-containing building blocks is of interest due to their utility as synthetic intermediates and their prevalence in pharmaceuticals. As a result, significant efforts have been made to develop methods to access these motifs which rely on safer and non-toxic sources of CN. Herein, we report that 2-methyl-2-phenylpropanenitrile is an efficient, non-toxic, electrophilic CN source for the synthesis of nitrile-bearing quaternary centers via a thermodynamic transnitrilation and anion-relay strategy. This one-pot process leads to nitrile products resulting from the gem-difunctionalization of alkyl lithium reagents.<br>

scholarly journals (2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol

Molbank ◽  
10.3390/m1140 ◽  
2020 ◽  
Vol 2020 (2) ◽  
pp. M1140
Author(s):  
Jack Bennett ◽  
Paul Murphy
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Ir Spectroscopy ◽  
13C Nmr ◽  
Conjugate Addition ◽  
13C Nmr Spectroscopy ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Esi Mass Spectrometry ◽  
The One

(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1,8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by 1H and 13C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.

scholarly journals Tandem Fries Reaction–Conjugate Addition under Microwave Irradiation in Dry Media; One-pot Synthesis of Flavanones

1999 ◽  
Vol 23 (9) ◽  
pp. 574-575
Author(s):  
Firouz Matloubi Moghaddam ◽  
Mohammad Ghaffarzadeh ◽  
Seyed Hossein Abdi-Oskoui
Keyword(s):  
Microwave Irradiation ◽  
Silica Gel ◽  
Conjugate Addition ◽  
Solvent Free ◽  
Naphthalene Derivatives ◽  
One Pot ◽  
Fries Rearrangement ◽  
One Pot Synthesis ◽  
Solvent Free Conditions ◽  
Fries Reaction

An AICl3–ZnCl2 mixture supported on silica gel is found to be an efficient medium for the Fries rearrangement of acyloxybenzene or naphthalene derivatives in solvent-free conditions under microwave irradiation.

Base-mediated sequential one-pot approach for the synthesis of 2,3-disubstituted indoles from 2-(tosylamino)aryl-substituted para-quinone methides

Tetrahedron ◽  
2021 ◽  
Vol 82 ◽  
pp. 131950
Author(s):  
Rajat Pandey ◽  
Gurdeep Singh ◽  
Vinod Gour ◽  
Ramasamy Vijaya Anand
Keyword(s):  
Quinone Methides ◽  
One Pot

Copper-catalyzed 1,6-conjugate addition of para-quinone methides with diborylmethane

2021 ◽  
Author(s):  
Xin Li ◽  
Guoliang Gao ◽  
Songtao He ◽  
Qiuling Song
Keyword(s):  
Catalytic System ◽  
Conjugate Addition ◽  
Quinone Methides ◽  
High Yields

Presented herein is the first 1,6-conjugate addition of diborylmethane, which is promoted by a simple and inexpensive copper catalytic system. This method features high yields, good selectivities and broad functional...

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