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

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2019 Aug 29

PMID 31457175

Citations 5

Authors

Angel Renteria-Gomez

Alejandro Islas-Jacome

Alicia E Cruz-Jimenez

Jessica C Manzano-Velazquez

Susana Rojas-Lima

J Oscar C Jimenez-Halla

Rocio Gamez-Montano

Affiliations

Soon will be listed here.

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/(Nacylation/-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.

Citing Articles

One-pot Ugi-azide and Heck reactions for the synthesis of heterocyclic systems containing tetrazole and 1,2,3,4-tetrahydroisoquinoline.

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Synthesis of Polyheterocyclic Dimers Containing Restricted and Constrained Peptidomimetics via IMCR-Based Domino/Double CuAAC Click Strategy.

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Renteria-Gomez M, Islas-Jacome A, Pharande S, Vosburg D, Gamez-Montano R Front Chem. 2019; 7:546.

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Solvent- and Catalyst-Free One-Pot Green Bound-Type Fused Bis-Heterocycles Synthesis via Groebke-Blackburn-Bienaymé Reaction/SAr/Ring-Chain Azido-Tautomerization Strategy.

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