Unexpected formal [4 + 2]-cycloaddition of chalcone imines and homophthalic anhydrides: preparation of dihydropyridin-2(1H)-ones-Reference-Cited by-同舟云学术

Unexpected formal [4 + 2]-cycloaddition of chalcone imines and homophthalic anhydrides: preparation of dihydropyridin-2(1H)-ones

Published:2021 Issue:17 Volume:19 Page:3829-3833
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Guranova Natalia¹²³,Golubev Pavel¹²³,Bakulina Olga¹²³^ORCID,Dar'in Dmitry¹²³,Kantin Grigory¹²³,Krasavin Mikhail¹²³^ORCID

Affiliation:

1. Saint Petersburg State University

2. Saint Petersburg

3. 199034 Russian Federation

Abstract

Chalcone imines were reacted with homophthalic anhydrides to serve as a four-atom building block in a [4+2]-formal cycloaddition reaction with unexpected chemoselectivity (Castagnoli–Cushman-type reaction), providing dihydropyridin-2(1H)-ones.

Funder

Russian Science Foundation

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2021/OB/D1OB00534K

Reference22 articles.

1. Recent advances in synthetic applications of azadienes

2. Pyridine synthesis by [4 + 2] cycloadditions of 1-azadienes: hetero-Diels Alder and transition metal-catalysed approaches

3. Diels-Alder reactions of 1-azadienes

4. Novel synthesis of sulfur-containing bicyclic β-lactams (thiaisoalkanams) using sulfur dichloride as a sulfur transfer reagent

5. Pyrrole and Oligopyrrole Synthesis by 1,3-Dipolar Cycloaddition of Azomethine Ylides with Sulfonyl Dipolarophiles

Cited by 7 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Concise Approach towards Tetramic Acid Derivatives via Ugi Reaction/Dieckmann Cyclization Sequence;ChemistrySelect;2024-02-22

2. Revisiting the 1,3-azadiene-succinic anhydride annulation reaction for the stereocontrolled synthesis of allylic 2-oxopyrrolidines bearing up to four contiguous stereocenters;RSC Advances;2024

3. Highly Selective Cyclization and Isomerization of Propargylamines to Access Functionalized Quinolines and 1-Azadienes;Molecules;2023-08-26

4. The Castagnoli–Cushman Reaction;Molecules;2023-03-15

5. The Use of Aryl-Substituted Homophthalic Anhydrides in the Castagnoli–Cushman Reaction Provides Access to Novel Tetrahydroisoquinolone Carboxylic Acid Bearing an All-Carbon Quaternary Stereogenic Center;Molecules;2022-12-02