Formal [4+2] cycloaddition of quinolines, pyridines, and isoquinolines with 3-ethoxycyclobutanones

Onnagawa, Tatsuo; Shima, Yusuke; Yoshimura, Tetsuzo; Matsuo, Jun‐ichi

doi:10.1016/j.tetlet.2016.06.011

Cited by 11 publications

(1 citation statement)

References 29 publications

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“…135 Discussed herein are only examples reported afterward (Table 2). 3-Alkoxycyclobutanone 287 undergoes formal (4 + 2) cycloaddition reactions with quinoline 291, 136 azobenzene 293, 137 and ynamide 295. 138 A reaction of α-monosubstituted alkoxycyclobutanone 297 with nitorosobenzene 298 was developed as well.…”

Section: Lewis Acid-mediated Ring-openingmentioning

confidence: 99%

Cleavage of Carbon–Carbon σ-Bonds of Four-Membered Rings

2020

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This article reviews synthetic transformations involving cleavage of a carbon− carbon bond of a four-membered ring, with a particular focus on the examples reported during the period from 2011 to the end of 2019. Most significant is the progress of catalytic reactions involving oxidative addition of carbon−carbon bonds onto transition metals or β-carbon elimination of transition metal alkoxides. When they are looked at from synthetic perspectives, they offer unique and efficient methods to build complex natural products and structures that are difficult to construct by conventional methods. On the other hand, β-scission of radical intermediates has also attracted increasing attention as an alternative elementary step to cleave carbon−carbon bonds. Its site-selectivity is often complementary to that of transition metalcatalyzed reactions. In addition, Lewis acid-mediated and thermally induced ring-opening of cyclobutanone derivatives has garnered renewed attention. On the whole, these examples demonstrate unique synthetic potentials of structurally strained four-membered ring compounds for the construction of organic skeletons.

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Section: Lewis Acid-mediated Ring-openingmentioning

confidence: 99%

Cleavage of Carbon–Carbon σ-Bonds of Four-Membered Rings

2020

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Lewis Acid‐Mediated [3+3] Annulation for the Construction of Substituted Pyrimidine and Pyridine Derivatives

2017

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Lewis‐acid Promoted Chemoselective Condensation of 2‐Aminobenzimidazoles or 3‐Aminoindazoles with 3‐Ethoxycyclobutanones to Construct Fused Nitrogen heterocycles

2018

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A Lewis-acid promoted chemoselective condensation of 2-aminobenzimidazoles or 3-aminoindazoles with 3-ethoxycyclobutanones is presented. Diverse fused heterocycles benzo[4,5]-imidazo[1,2-a]pyrimidine and pyrimido[1,2-b]-indazole derivatives were obtained in moderate to high yields under mild conditions, the reaction mechanism of which was in sharp contrast to previous [3 + 3] annulation reaction of 3-ethoxycyclobutanones.

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Formal [4+2] cycloaddition of quinolines, pyridines, and isoquinolines with 3-ethoxycyclobutanones

Cited by 11 publications

References 29 publications

Cleavage of Carbon–Carbon σ-Bonds of Four-Membered Rings

Cleavage of Carbon–Carbon σ-Bonds of Four-Membered Rings

Lewis Acid‐Mediated [3+3] Annulation for the Construction of Substituted Pyrimidine and Pyridine Derivatives

Lewis‐acid Promoted Chemoselective Condensation of 2‐Aminobenzimidazoles or 3‐Aminoindazoles with 3‐Ethoxycyclobutanones to Construct Fused Nitrogen heterocycles

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