Mn(III)-Mediated Cascade Cyclization of 1-(Azidomethyl)-2-Isocyanoarenes with Organoboronic acids: Construction of Quinazoline Derivatives

2021 ◽  
Author(s):  
Noor Shahina Begum ◽  
Yogesh Kumar Gujjenahalli Ramalingaiah
Keyword(s):  
Boronic Acid ◽  
Cascade Reaction ◽  
Single Electron ◽  
Cascade Cyclization ◽  
Organoboronic Acids ◽  
Radical Cascade ◽  
Quinazoline Derivatives

A novel and efficient Mn(III)-mediated oxidative radical cascade reaction of 1-(azidomethyl)-2-isocyanoarenes with organoboronic acids is reported. The single electron oxidation of a commercially available organo boronic acid in presence of...

Catalytic Radical Cascade Cyclization of Alkene-Tethered Enones to Fused Bicyclic Cyclopropanols

2021 ◽  
Author(s):  
Ying Xie ◽  
Wei Huang ◽  
Song Qin ◽  
Shaomin Fu ◽  
Bo Liu
Keyword(s):  
Hydrogen Atom ◽  
Cascade Reaction ◽  
Hydrogen Atom Transfer ◽  
Atom Transfer ◽  
Trimethyl Borate ◽  
Cascade Cyclization ◽  
Radical Cascade ◽  
Privileged Scaffolds

An unprecedented hydrogen atom transfer-triggered intramolecular cascade reaction between alkene and enone is developed, using Fe(acac)3, PhSiH2(Oi-Pr) and trimethyl borate, to efficiently construct cis-fused bicyclic cyclopropanols, privileged scaffolds often found...

scholarly journals Metal-free synthesis of 1,N6-ethenoadenines from N6-propargyl-adenines via NIS mediated radical cascade reaction

RSC Advances ◽  
2019 ◽  
Vol 9 (66) ◽  
pp. 38897-38901
Author(s):  
Ruchun Yang ◽  
Si Deng ◽  
Xiang-you Dong ◽  
Xianrong Song ◽  
Hu Cai ◽  
...  
Keyword(s):  
Cascade Reaction ◽  
Metal Free ◽  
Efficient Approach ◽  
Cascade Cyclization ◽  
Radical Cascade

An efficient approach for the construction of 1,N6-ethenoadenines is developed through the metal-free mediated radical cascade cyclization of conveniently prepared N6-propargyl-adenines.

Fe-Catalyzed Conjunctive Cross-Couplings of Unactivated Alkenes with Grignard Reagents

2020 ◽  
Author(s):  
Lei Liu ◽  
Wes Lee ◽  
Cassandra R. Youshaw ◽  
Mingbin Yuan ◽  
Michael B. Geherty ◽  
...  
Keyword(s):  
Functional Groups ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Turnover Frequency ◽  
Diverse Range ◽  
Cascade Cyclization ◽  
Radical Cascade

The first iron-catalyzed three-component cross-coupling of unactivated olefins with alkyl halides and Grignard reagents is reported. The reaction operates under fast turnover frequency and tolerates a diverse range of sp2-hybridized nucleophiles, alkyl halides, and unactivated olefins bearing diverse functional groups to yield the desired 1,2-alkylarylated products with high regiocontrol. Further, we demonstrate that this protocol is amenable for the synthesis of new (hetero)carbocycles including tetrahydrofurans and pyrrolidines via a three-component radical cascade cyclization/arylation that forges three new C-C bonds.

A metal-free radical cascade reaction of phosphine oxides with 2-aryloxy phenylacetylenes to assemble diphosphonyl xanthene derivatives

2021 ◽  
Author(s):  
Tao Fan ◽  
Yan Liu ◽  
Caina Jiang ◽  
Yanli Xu ◽  
Yan-Yan Chen
Keyword(s):  
Free Radical ◽  
Transition Metal ◽  
Cascade Reaction ◽  
Phosphine Oxides ◽  
Metal Free ◽  
Mild Conditions ◽  
Xanthene Derivatives ◽  
Reaction Proceeds ◽  
Radical Cascade

A radical cascade reaction of 2-aryloxy phenylacetylene with phosphine oxides promoted by K2S2O8 was developed, provided diphosphonyl xanthenes as products. This reaction proceeds under transition metal-free and mild conditions with...

Highly Cumulated Radical Cascade Reaction of aza-1,6-Enyenes: Stereoselective Synthesis of exo -Methylene Piperidines

2020 ◽  
Vol 2020 (11) ◽  
pp. 1700-1707
Author(s):  
Akio Kamimura ◽  
Tomoyuki Itaya ◽  
Tatsuro Yoshinaga ◽  
Ryo Nozawa ◽  
Takuji Kawamoto ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Cascade Reaction ◽  
Radical Cascade

Eosin Y photoredox catalyzed net redox neutral reaction for regiospecific annulation to 3-sulfonylindoles via anion oxidation of sodium sulfinate salts

2018 ◽  
Vol 16 (4) ◽  
pp. 536-540 ◽  
Author(s):  
Rajendra S. Rohokale ◽  
Shrikant D. Tambe ◽  
Umesh A. Kshirsagar
Keyword(s):  
Visible Light ◽  
Eosin Y ◽  
Cascade Cyclization ◽  
Neutral Reaction ◽  
Neutral Process ◽  
Radical Cascade

An eosin Y photoredox catalyzed net redox neutral process for 3-sulfonylindoles via the anionic oxidation of sodium sulfinate salts and its radical cascade cyclization with 2-alkynyl-azidoarenes was developed with visible light as a mediator.

scholarly journals Preparation of optically active bicyclodihydrosiloles by a radical cascade reaction

2013 ◽  
Vol 9 ◽  
pp. 1326-1332 ◽  
Author(s):  
Koichiro Miyazaki ◽  
Yu Yamane ◽  
Ryuichiro Yo ◽  
Hidemitsu Uno ◽  
Akio Kamimura
Keyword(s):  
Silicon Atom ◽  
Cascade Reaction ◽  
Radical Cyclization ◽  
Optically Active ◽  
Unsaturated Ester ◽  
Terminal Alkyne ◽  
Silyl Radical ◽  
Vinyl Radical ◽  
Radical Cascade ◽  
Carbonyl Radical

Bicyclodihydrosiloles were readily prepared from optically active enyne compounds by a radical cascade reaction triggered by tris(trimethylsilyl)silane ((Me3Si)3SiH). The reaction was initiated by the addition of a silyl radical to an α,β-unsaturated ester, forming an α-carbonyl radical that underwent radical cyclization to a terminal alkyne unit. The resulting vinyl radical attacked the silicon atom in an SHi manner to give dihydrosilole. The reaction preferentially formed trans isomers of bicyclosiloles with an approximately 7:3 to 9:1 selectivity.

scholarly journals Biomimetic Synthesis of Hitorins A and B via an Intermolecular Alkoxy Radical-Olefin Coupling Cascade

2019 ◽  
Author(s):  
Xiaohuan Li ◽  
Tianran Zhai ◽  
Ping He ◽  
Zheng Wei ◽  
Zhang Wang
Keyword(s):  
Cascade Reaction ◽  
Oxidative Cleavage ◽  
Experimental Results ◽  
Biomimetic Synthesis ◽  
Alkoxy Radical ◽  
Radical Oxidation ◽  
Olefin Coupling ◽  
Radical Cascade ◽  
Grob Fragmentation

A biomimetic synthesis of hitorins A and B was achieved based on our modified biosynthetic proposal. In our synthesis, a radical cascade reaction between an alkoxy radical, generated from a hydroperoxide, and a monoterpene (+)-sabinene renders the tetrahydrofuran ring of hitorins A and B. In addition, experimental results supported that the oxidative cleavage of the tetrasubstituted olefin in a key intermediate is via a radical oxidation cascade followed by a Grob fragmentation.<br>

Iron-catalyzed radical cascade cyclization of oxime esters with isocyanides: synthesis of 1-cyanoalkyl isoquinolines and 6-cyanoalkyl phenanthridines

2021 ◽  
Vol 19 (39) ◽  
pp. 8597-8606
Author(s):  
Dengqi Xue ◽  
Rongqi Liu ◽  
Denggao Zhang ◽  
Ning Li ◽  
Yijie Xue ◽  
...  
Keyword(s):  
Cascade Cyclization ◽  
Radical Cascade

An iron-catalyzed radical cascade cyclization of oxime esters with isocyanides for the synthesis of 1-cyanoalkyl isoquinolines and 6-cyanoalkyl phenanthridines has been developed.

Electrochemical oxidative radical cascade cyclization of olefinic amides and thiophenols towards the synthesis of sulfurated benzoxazines, oxazolines and iminoisobenzofurans

2021 ◽  
Author(s):  
Fangling Lu ◽  
Jie Xu ◽  
Hao Li ◽  
Ke Wang ◽  
Dandan Ouyang ◽  
...  
Keyword(s):  
Cascade Cyclization ◽  
Radical Cascade

Heterocycles containing N and O are important structures in pharmaceuticals, agrochemicals and functional molecules.

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