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Synthesis of 2-Tetrazolylmethyl-isoindolin-1-ones via a One-Pot Ugi-Azide/(N-Acylation/exo-Diels-Alder)/Dehydration Process.


ABSTRACT: A series of fifteen 2-tetrazolylmethyl-isoindolin-1-one linked-type bis-heterocycles were synthesized in 10-76% yields under mild conditions via a one-pot Ugi-azide/(N-acylation/exo-Diels-Alder)/dehydration process from furan-2-ylmethanamine, aldehydes, isocyanides, azidotrimethylsilane, and maleic anhydride. Density functional theory calculations were performed using the polarizable continuum model (toluene)-M06-2X-D3/6-311+G(d)//M06-2X-D3/6-31G(d) level of theory to obtain the full energy profile when investigating over eight possible pathways. An anthracene-containing analogue displayed a distribution of its highest occupied molecular orbital-lowest unoccupied molecular orbital throughout both cyclic moieties.

SUBMITTER: Renteria-Gomez A 

PROVIDER: S-EPMC6640813 | biostudies-literature | 2016 Nov

REPOSITORIES: biostudies-literature

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Synthesis of 2-Tetrazolylmethyl-isoindolin-1-ones via a One-Pot Ugi-Azide/(N-Acylation/<i>exo</i>-Diels-Alder)/Dehydration Process.

Rentería-Gómez Angel A   Islas-Jácome Alejandro A   Cruz-Jiménez Alicia E AE   Manzano-Velázquez Jessica C JC   Rojas-Lima Susana S   Jiménez-Halla J Oscar C JOC   Gámez-Montaño Rocío R  

ACS omega 20161116 5


A series of fifteen 2-tetrazolylmethyl-isoindolin-1-one linked-type bis-heterocycles were synthesized in 10-76% yields under mild conditions via a one-pot Ugi-azide/(N<i>-</i>acylation/<i>exo</i>-Diels-Alder)/dehydration process from furan-2-ylmethanamine, aldehydes, isocyanides, azidotrimethylsilane, and maleic anhydride. Density functional theory calculations were performed using the polarizable continuum model (toluene)-M06-2X-D3/6-311+G(d)//M06-2X-D3/6-31G(d) level of theory to obtain the fu  ...[more]

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