Acetylene-based two-step diastereoselective synthesis of bridgehead dihydro-oxadiazines using ketones and hydrazine as the only reactants

2019 ◽  
Vol 55 (18) ◽  
pp. 2632-2635 ◽  
Author(s):  
Elena Yu. Schmidt ◽  
Nadezhda V. Semenova ◽  
Elena V. Ivanova ◽  
Inna V. Tatarinova ◽  
Igor’ A. Ushakov ◽  
...  
Keyword(s):  
Self Organization ◽  
Diastereoselective Synthesis ◽  
Diastereoselective Reaction ◽  
Acid Catalyzed

Bridgehead dihydro-1,3,4-oxadiazines are synthesized by the acid-catalyzed diastereoselective reaction of hydrazine with 6,8-dioxabicyclo[3.2.1]octanes, the products of the superbase-promoted self-organization of acetylene with ketones.

Naturally Occurring Organic Acid-catalyzed Facile Diastereoselective Synthesis of Biologically Active (E)-3-(arylimino)indolin-2-one Derivatives in Water at Room Temperature

2019 ◽  
Vol 23 (16) ◽  
pp. 1778-1788 ◽  
Author(s):  
Gurpreet Kaur ◽  
Arvind Singh ◽  
Kiran Bala ◽  
Mamta Devi ◽  
Anjana Kumari ◽  
...  
Keyword(s):  
Room Temperature ◽  
Biologically Active ◽  
Environmentally Benign ◽  
Diastereoselective Synthesis ◽  
Substituted Anilines ◽  
Reaction Conditions ◽  
Naturally Occurring ◽  
Acid Catalyzed ◽  
Reaction Media ◽  
Column Chromatographic

A simple, straightforward and efficient method has been developed for the synthesis of (E)-3-(arylimino)indolin-2-one derivatives and (E)-2-((4-methoxyphenyl)imino)- acenaphthylen-1(2H)-one. The synthesis of these biologically-significant scaffolds was achieved from the reactions of various substituted anilines and isatins or acenaphthaquinone, respectively, using commercially available, environmentally benign and naturally occurring organic acids such as mandelic acid or itaconic acid as catalyst in aqueous medium at room temperature. Mild reaction conditions, energy efficiency, good to excellent yields, environmentally benign conditions, easy isolation of products, no need of column chromatographic separation and the reusability of reaction media are some of the significant features of the present protocol.

Diastereoselective Synthesis of Cycloheptannelated Indoles via Lewis-Acid-Catalyzed (4 + 3)-Cyclization of Donor–Acceptor Cyclopropanes

2020 ◽  
Vol 22 (5) ◽  
pp. 1903-1907 ◽  
Author(s):  
Bao Qiong Li ◽  
Zong-Wang Qiu ◽  
Ai-Jun Ma ◽  
Jin-Bao Peng ◽  
Na Feng ◽  
...  
Keyword(s):  
Lewis Acid ◽  
Diastereoselective Synthesis ◽  
Donor Acceptor ◽  
Acid Catalyzed

Chiral phosphoric acid catalyzed atroposelective and diastereoselective synthesis of 9-aryltetrahydroacridines

2020 ◽  
Vol 7 (16) ◽  
pp. 2255-2262 ◽  
Author(s):  
You-Dong Shao ◽  
Dan-Dan Han ◽  
Wen-Yue Ma ◽  
Dao-Juan Cheng
Keyword(s):  
Phosphoric Acid ◽  
Diastereoselective Synthesis ◽  
Chiral Phosphoric Acid ◽  
Axially Chiral ◽  
Acid Catalyzed

A chiral phosphoric acid catalyzed atroposelective annulation between 2-aminoaryl ketones and alicyclic ketones has been developed to access a new library of enantioenriched axially chiral 9-aryltetrahydroacridines.

scholarly journals Highly diastereoselective synthesis of tricyclic fused-pyrans by sequential hydride shift mediated double C(sp3)–H bond functionalization

2018 ◽  
Vol 9 (37) ◽  
pp. 7327-7331 ◽  
Author(s):  
Keiji Mori ◽  
Nobuaki Umehara ◽  
Takahiko Akiyama
Keyword(s):  
Bronsted Acid ◽  
Brønsted Acid ◽  
Diastereoselective Synthesis ◽  
Bond Functionalization ◽  
Hydride Shift ◽  
Brönsted Acid ◽  
Acid Catalyzed

Highly diastereoselective synthesis of tricyclic fused-pyrans was achieved by Brønsted acid catalyzed double C(sp3)–H bond functionalization.

Lewis acid catalyzed diastereoselective [3+4]-annulation of donor–acceptor cyclopropanes with anthranils: synthesis of tetrahydro-1-benzazepine derivatives

2017 ◽  
Vol 53 (61) ◽  
pp. 8521-8524 ◽  
Author(s):  
Zhe-Hao Wang ◽  
Huan-Huan Zhang ◽  
Dao-Ming Wang ◽  
Peng-Fei Xu ◽  
Yong-Chun Luo
Keyword(s):  
Lewis Acid ◽  
Diastereoselective Synthesis ◽  
Donor Acceptor ◽  
Acid Catalyzed

The [3+4]-annulation between donor–acceptor cyclopropanes and anthranils has been developed for the diastereoselective synthesis of tetrahydro-1-benzazepine derivatives.

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