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

Ángel RenteríaGómez | Zendy; Alejandro IslasJácome | Zendy; Alicia E. Cruz-Jiménez | Zendy; Jessica C. Manzano-Velázquez | Zendy; Susana RojasLima | Zendy; J. Óscar C. JiménezHalla | Zendy; Rocío GámezMontaño | Zendy

Open Access

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

Author(s) -

Ángel RenteríaGómez,

Alejandro IslasJácome,

Alicia E. Cruz-Jiménez,

Jessica C. Manzano-Velázquez,

Susana RojasLima,

J. Óscar C. JiménezHalla,

Rocío GámezMontaño

Publication year - 2016

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.6b00281

Subject(s) - chemistry , azide , maleic anhydride , dehydration , acylation , molecular orbital , density functional theory , diels–alder reaction , homo/lumo , medicinal chemistry , computational chemistry , organic chemistry , molecule , biochemistry , copolymer , catalysis , polymer

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.

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