Literature DB >> 33389558

An efficient diastereoselective synthesis of novel fused 5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-ones via one-pot three-component reaction.

Tooba Tabibi1, Abbas Ali Esmaeili2, Joel T Mague3.   

Abstract

Herein, a convenient and efficient synthesis of 7-benzoyl-6-(aryl)-6,7-dihydro-5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-one derivatives was achieved from the reaction of isoquinolinium N-ylides, aromatic aldehydes, and heterocyclic 1,3-dicarbonyl compounds via one-pot three-component diastereoselective domino reaction in good-to-excellent yields. The advantages of this protocol are easily available starting materials, operational simplicity, and avoidance of hazardous organic solvents and catalyst. The synthesized products were characterized by IR, 1H NMR, 13C NMR and mass spectra. Additionally, the conclusive structure of target compounds was confirmed by X-Ray diffraction analysis.
© 2021. The Author(s), under exclusive licence to Springer Nature Switzerland AG part of Springer Nature.

Entities:  

Keywords:  7-benzoyl-6-(aryl)-6,7-dihydro-5H-furo[2,3-d]thiazolo[3,2-a]pyrimidin-5-one; Isoquinoline; Phenacyl bromide; Thiazolo[3,2-a]pyrimidin; Three-component reaction

Mesh:

Year:  2021        PMID: 33389558     DOI: 10.1007/s11030-020-10173-4

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


  19 in total

1.  Synthesis and biological evaluation of 6-(alkyn-1-yl)furo[2,3-d]pyrimidin-2(3H)-one base and nucleoside derivatives.

Authors:  Morris J Robins; Karl Miranda; Vivek K Rajwanshi; Matt A Peterson; Graciela Andrei; Robert Snoeck; Erik De Clercq; Jan Balzarini
Journal:  J Med Chem       Date:  2006-01-12       Impact factor: 7.446

2.  Synthesis of classical, three-carbon-bridged 5-substituted furo[2,3-d]pyrimidine and 6-substituted pyrrolo[2,3-d]pyrimidine analogues as antifolates.

Authors:  Aleem Gangjee; Yibin Zeng; John J McGuire; Farideh Mehraein; Roy L Kisliuk
Journal:  J Med Chem       Date:  2004-12-30       Impact factor: 7.446

3.  Synthesis and biological evaluation of acyclic 3-[(2-hydroxyethoxy)methyl] analogues of antiviral furo- and pyrrolo[2,3-d]pyrimidine nucleosides.

Authors:  Zlatko Janeba; Jan Balzarini; Graciela Andrei; Robert Snoeck; Erik De Clercq; Morris J Robins
Journal:  J Med Chem       Date:  2005-07-14       Impact factor: 7.446

4.  Effect of C9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines.

Authors:  A Gangjee; Y Zeng; J J McGuire; R L Kisliuk
Journal:  J Med Chem       Date:  2000-08-10       Impact factor: 7.446

5.  Synthesis and antiviral activity of novel acyclic nucleosides in the 5-alkynyl- and 6-alkylfuro[2,3-d]pyrimidine series.

Authors:  Franck Amblard; Vincent Aucagne; Pierre Guenot; Raymond F Schinazi; Luigi A Agrofoglio
Journal:  Bioorg Med Chem       Date:  2005-02-15       Impact factor: 3.641

6.  Novel 5-substituted, 2,4-diaminofuro[2,3-d]pyrimidines as multireceptor tyrosine kinase and dihydrofolate reductase inhibitors with antiangiogenic and antitumor activity.

Authors:  Aleem Gangjee; Yibin Zeng; Michael Ihnat; Linda A Warnke; Dixy W Green; Roy L Kisliuk; Fu-Tyan Lin
Journal:  Bioorg Med Chem       Date:  2005-09-15       Impact factor: 3.641

7.  Synthesis of classical, four-carbon bridged 5-substituted furo[2,3-d]pyrimidine and 6-substituted pyrrolo[2,3-d]pyrimidine analogues as antifolates.

Authors:  Aleem Gangjee; Yibin Zeng; John J McGuire; Roy L Kisliuk
Journal:  J Med Chem       Date:  2005-08-11       Impact factor: 7.446

8.  Rational design of 4-amino-5,6-diaryl-furo[2,3-d]pyrimidines as potent glycogen synthase kinase-3 inhibitors.

Authors:  Yasushi Miyazaki; Yutaka Maeda; Hideyuki Sato; Masato Nakano; Geoffrey W Mellor
Journal:  Bioorg Med Chem Lett       Date:  2008-02-02       Impact factor: 2.823

9.  Classical and nonclassical furo[2,3-d]pyrimidines as novel antifolates: synthesis and biological activities.

Authors:  A Gangjee; R Devraj; J J McGuire; R L Kisliuk; S F Queener; L R Barrows
Journal:  J Med Chem       Date:  1994-04-15       Impact factor: 7.446

10.  Design, synthesis, and X-ray crystal structures of 2,4-diaminofuro[2,3-d]pyrimidines as multireceptor tyrosine kinase and dihydrofolate reductase inhibitors.

Authors:  Aleem Gangjee; Wei Li; Lu Lin; Yibin Zeng; Michael Ihnat; Linda A Warnke; Dixy W Green; Vivian Cody; Jim Pace; Sherry F Queener
Journal:  Bioorg Med Chem       Date:  2009-08-22       Impact factor: 3.641

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