Tandem One-Pot Approach To Access 1,2,3-Triazole-fused Isoindolines through Cu-Catalyzed 1,6-Conjugate Addition of Me3SiN3top-Quinone Methides followed by Intramolecular Click Cycloaddition

2018 ◽  
Vol 83 (15) ◽  
pp. 8596-8606 ◽  
Author(s):  
Abhijeet S. Jadhav ◽  
Yogesh A. Pankhade ◽  
Ramasamy Vijaya Anand
Keyword(s):  
Conjugate Addition ◽  
Quinone Methides ◽  
One Pot

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.

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.

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.

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...

Organocatalytic cascade 1,6-conjugate addition/annulation/tautomerization of functionalized para-quinone methides: Access to chiral 2-amino-4-aryl-4H-chromenes

2018 ◽  
Vol 29 (8) ◽  
pp. 1273-1276 ◽  
Author(s):  
Cong Duan ◽  
Ling Ye ◽  
Wenqin Xu ◽  
Xinying Li ◽  
Feng Chen ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Quinone Methides

Organometallics in prostaglandin synthesis

1988 ◽  
Vol 326 (1592) ◽  
pp. 579-585 ◽  
Keyword(s):  
Conjugate Addition ◽  
Prostaglandin Synthesis ◽  
Side Chain ◽  
Prostaglandin E ◽  
Controlled Synthesis ◽  
One Pot ◽  
Naturally Occurring ◽  
Chain Unit ◽  
Alkyl Iodides

An extremely short way to prostaglandins has been opened by combining the newly devised organometallic methodologies. Convergent, one-pot creation of the prostanoid framework is achieved by organocopper conjugate addition of the S-configurated ω-side-chain unit to (R)-4-trialkylsiloxy-2-cyclopentenone followed by the organotin-aided trapping of the enolate intermediate by α-side-chain alkyl iodides. Prostaglandin E 2 can be prepared in only three steps from the chiral building units. The protected 5,6-didehydro-PGE 2 derivatives thus obtained serve as common intermediates for the synthesis of a variety of naturally occurring prostaglandins including prostacyclin. This approach is also useful for the controlled synthesis of isocarbacyclin.

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