An efficient synthesis of 4H-chromene, 4H-pyran, and oxepine derivatives via one-pot three-component tandem reactions

A new and efficient method has been developed for the synthesis of highly functionalized 2-amino-4H-pyran, 2-amino-4H-chromene, 2-amino-oxepine, and 2-hydroxy-oxepine derivatives through one-pot, three-component tandem reactions of structurally diverse 1,3-diketones, dialkyl acetylenedicarboxylates,...

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Veröffentlicht in:Tetrahedron letters 2012-12, Vol.53 (51), p.6977-6981
Hauptverfasser: Kazemi, Bagher, Javanshir, Shahrzad, Maleki, Ali, Safari, Mostafa, Khavasi, Hamid Reza
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container_end_page 6981
container_issue 51
container_start_page 6977
container_title Tetrahedron letters
container_volume 53
creator Kazemi, Bagher
Javanshir, Shahrzad
Maleki, Ali
Safari, Mostafa
Khavasi, Hamid Reza
description A new and efficient method has been developed for the synthesis of highly functionalized 2-amino-4H-pyran, 2-amino-4H-chromene, 2-amino-oxepine, and 2-hydroxy-oxepine derivatives through one-pot, three-component tandem reactions of structurally diverse 1,3-diketones, dialkyl acetylenedicarboxylates, and malononitrile or ethyl cyanoacetate in the presence of a catalytic amount of Na2CO3 in ethanol. This efficient technique has the advantages of giving products in good to high yields, in short reaction times, and with a simple isolation procedure.
doi_str_mv 10.1016/j.tetlet.2012.10.046
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source Elsevier ScienceDirect Journals
subjects Cascade chemical reactions
Catalysis
Chromene
Derivatives
Dialkyl acetylenedicarboxylate
Ethanol
Ethyl alcohol
Malononitrile
Multicomponent reaction
Oxepine
Pyran
Reaction time
Synthesis (chemistry)
Tetrahedrons
title An efficient synthesis of 4H-chromene, 4H-pyran, and oxepine derivatives via one-pot three-component tandem reactions
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