Literature DB >> 17385876

One-pot, multicomponent route to pyrazoloquinolizinones.

Valentin A Chebanov1, Vyacheslav E Saraev, Sergey M Desenko, Vitaliy N Chernenko, Svetlana V Shishkina, Oleg V Shishkin, Kiril M Kobzar, C Oliver Kappe.   

Abstract

[reaction: see text] An efficient synthesis of 5a-hydroxy-4,5,5a,6,7,8-hexahydropyrazolo[4,3-c]quinolizin-9-ones based on the three-component condensation of 5-aminopyrazoles, aromatic aldehydes, and cyclic 1,3-diketones is described. The multicomponent reaction is performed under strongly basic conditions applying controlled microwave heating in a sealed vessel and involves an unusual base-mediated ring-opening/recyclization of the cyclic 1,3-diketone moiety.

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Year:  2007        PMID： 17385876     DOI： 10.1021/ol070411l

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

Review 1.  Recent developments in utility of green multi-component reactions for the efficient synthesis of polysubstituted pyrans, thiopyrans, pyridines, and pyrazoles.

Authors:  Mohamed Hilmy Elnagdi; Moustafa Sherief Moustafa; Saleh Mohammed Al-Mousawi; Ramadan Ahmed Mekheimer; Kamal Usef Sadek
Journal:  Mol Divers       Date:  2015-04-17       Impact factor: 2.943

2.  Diversity oriented heterocyclizations of pyruvic acids, aldehydes and 5-amino-N-aryl-1H-pyrazole-4-carboxamides: catalytic and temperature control of chemoselectivity.

Authors:  Yana I Sakhno; Svetlana V Shishkina; Oleg V Shishkin; Vladimir I Musatov; Elena V Vashchenko; Sergey M Desenko; Valentin A Chebanov
Journal:  Mol Divers       Date:  2010-03-14       Impact factor: 2.943

3.  Spectroscopic Physicochemical and Photophysical Investigation of Biologically Active 2-oxo-quinoline-3-carbonitrile Derivative.

Authors:  Mohie E M Zayed; Parveen Kumar
Journal:  J Fluoresc       Date:  2017-01-21       Impact factor: 2.217

4.  Enantioselective organocatalytic Hantzsch synthesis of polyhydroquinolines.

Authors:  Christopher G Evans; Jason E Gestwicki
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005

5.  5-(4-Chloro-phen-yl)-1-methyl-3-phenyl-3,6,8,9-tetra-hydro-pyrazolo-[3,4-b]thio-pyrano[4,3-d]pyridine.

Authors:  Runhong Jia; Juhua Peng
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-08-27

6.  Regioselectivity in the multicomponent reaction of 5-aminopyrazoles, cyclic 1,3-diketones and dimethylformamide dimethylacetal under controlled microwave heating.

Authors:  Kamal Usef Sadek; Ramadan Ahmed Mekheimer; Tahany Mahmoud Mohamed; Moustafa Sherief Moustafa; Mohamed Hilmy Elnagdi
Journal:  Beilstein J Org Chem       Date:  2012-01-04       Impact factor: 2.883

Review 7.  Microwave multicomponent synthesis.

Authors:  Helmut M Hügel
Journal:  Molecules       Date:  2009-12-01       Impact factor: 4.411

8.  Pyridine-2-carboxylic acid as an effectual catalyst for rapid multi-component synthesis of pyrazolo[3,4-b]quinolinones.

Authors:  Mayank G Sharma; Ruturajsinh M Vala; Hitendra M Patel
Journal:  RSC Adv       Date:  2020-09-25       Impact factor: 4.036

9.  Features of the behavior of 4-amino-5-carboxamido-1,2,3-triazole in multicomponent heterocyclizations with carbonyl compounds.

Authors:  Eugene S Gladkov; Katerina A Gura; Svetlana M Sirko; Sergey M Desenko; Ulrich Groth; Valentin A Chebanov
Journal:  Beilstein J Org Chem       Date:  2012-11-30       Impact factor: 2.883

Review 10.  Recent advances in the chemistry of imine-based multicomponent reactions (MCRs).

Authors:  Lokman H Choudhury; Tasneem Parvin
Journal:  Tetrahedron       Date:  2011-07-18       Impact factor: 2.457
  10 in total

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