Literature DB >> 32008141

Dipolar cycloaddition strategy for three-component synthesis of chromeno[3',4':3,4]pyrido[2,1-a]isoquinoline derivatives.

Abdolali Alizadeh1, Parinaz Jamal2, Atefeh Roosta2, Reza Rezaiyehraad2, Tian-Fu Liu3, Mojtaba Khanpour3.   

Abstract

A rapid and efficient protocol to fused pentacyclic compounds, the chromeno[3',4':3,4]pyrido[2,1-a]isoquinolines, via a diastereoselective 1,4-dipolar cycloaddition reaction of isoquinoline, dialkyl acetylenedicarboxylates, and 3-acetyl coumarins, is described.

Entities:  

Keywords:  1,4-Dipolar cycloaddition reaction; 3-Acetyl coumarins; Chromeno[3′,4′:3,4]pyrido[2,1-a]isoquinoline; Dialkyl acetylenedicarboxylates; Diastereoselectivity; Fused pentacyclic compounds; Isoquinoline; Three-component reaction

Year:  2020        PMID： 32008141     DOI： 10.1007/s11030-020-10041-1

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   2.943


  10 in total

1.  Direct evaluation of secondary orbital interactions in the Diels-Alder reaction between cyclopentadiene and maleic anhydride.

Authors:  A Arrieta; F P Cossío; B Lecea
Journal:  J Org Chem       Date:  2001-09-07       Impact factor: 4.354

2.  Skeletal diverse synthesis of N-fused polycyclic heterocycles via the sequence of Ugi-type MCR and CuI-catalyzed coupling/tandem Pictet-Spengler reaction.

Authors:  Vikas Tyagi; Shahnawaz Khan; Vikas Bajpai; Harsh M Gauniyal; Brijesh Kumar; Prem M S Chauhan
Journal:  J Org Chem       Date:  2012-01-24       Impact factor: 4.354

Review 3.  Coumarin heterocyclic derivatives: chemical synthesis and biological activity.

Authors:  Fernanda G Medina; Joaquín G Marrero; Mariana Macías-Alonso; Magdalena C González; Iván Córdova-Guerrero; Ariana G Teissier García; Soraya Osegueda-Robles
Journal:  Nat Prod Rep       Date:  2015-09-23       Impact factor: 13.423

4.  Hyperconjugative, Secondary Orbital, Electrostatic, and Steric Effects on the Reactivities and Endo and Exo Stereoselectivities of Cyclopropene Diels-Alder Reactions.

Authors:  Brian J Levandowski; K N Houk
Journal:  J Am Chem Soc       Date:  2016-12-15       Impact factor: 15.419

5.  Facile synthesis of dispirooxindole-fused heterocycles via domino 1,4-dipolar addition and Diels-Alder reaction of in situ generated Huisgen 1,4-dipoles.

Authors:  Jing Sun; Yan Sun; Hui Gong; Ya-Jing Xie; Chao-Guo Yan
Journal:  Org Lett       Date:  2012-10-10       Impact factor: 6.005

6.  A novel three-component reaction for the diastereoselective synthesis of 2H-pyrimido[2,1-a]isoquinolines via 1,4-dipolar cycloaddition.

Authors:  Vijay Nair; A R Sreekanth; N Abhilash; Mohan M Bhadbhade; Rajesh C Gonnade
Journal:  Org Lett       Date:  2002-10-17       Impact factor: 6.005

7.  The existence of secondary orbital interactions.

Authors:  Chaitanya S Wannere; Ankan Paul; Rainer Herges; K N Houk; Henry F Schaefer; Paul von Ragué Schleyer
Journal:  J Comput Chem       Date:  2007-01-15       Impact factor: 3.376

8.  Iodine(V) reagents in organic synthesis. Part 1. Synthesis of polycyclic heterocycles via Dess-Martin periodinane-mediated cascade cyclization: generality, scope, and mechanism of the reaction.

Authors:  K C Nicolaou; P S Baran; Y-L Zhong; K Sugita
Journal:  J Am Chem Soc       Date:  2002-03-13       Impact factor: 15.419

9.  Tandem electrophilic cyclization-[3+2] cycloaddition-rearrangement reactions of 2-alkynylbenzaldoxime, DMAD, and Br2.

Authors:  Qiuping Ding; Zhiyong Wang; Jie Wu
Journal:  J Org Chem       Date:  2009-01-16       Impact factor: 4.354

10.  Solvent-free and room temperature synthesis of 3-arylquinolines from different anilines and styrene oxide in the presence of Al2O3/MeSO3H.

Authors:  Hashem Sharghi; Mahdi Aberi; Mohsen Khataminejad; Pezhman Shiri
Journal:  Beilstein J Org Chem       Date:  2017-09-20       Impact factor: 2.883
  10 in total

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