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.

A series of twelve new 1,5-disubstituted-1H-tetrazoles (1,5-DS-T) were synthesized by a MCR Ugiazide. The Ugi-azide products were obtained in moderate to excellent yields (50-96%). The 1,5-DS-T have in their structure a furan ring in linked manner. Both heterocycles are present in many biologically active products. 1,5-DS-T act like cis-amide bond bioisosters, while furan is used to optimize the solubility parameters and bioavailability of poorly soluble molecules.