Thiazolothiazoles. I. The Reaction of Aromatic Aldehydes with Dithioöxamide¹

Incorporating the Thiazolo[5,4-d]thiazole Unit into a Coordination Polymer with Interdigitated Structure

“…The heterocyclic thiazolo [5,4-d]thiazole (tztz) system ( Figure 1) experienced a renaissance in the last decade after it was first prepared by Ketcham et al in the 1960s [30]. The tztz unit was incorporated into photoactive materials due to its rigid and planar structure and electron deficiency.…”

One-pot microwave-assisted synthesis of 2,5-bis(pyrazol-4-yl)[1,3]thiazolo[5,4-d][1,3]thiazoles from pyrazole-4-carbaldehydes and dithiooxamide

“…Under the conditions reported in literature 18,30,34 or upon the reagents heating at 130 °C for 3 h in DMSO, the reaction mixture darkens and resinifies, only the initial aldehyde being detected among the reaction products.…”

“…29 Synthetic approaches to 2,5-disubstituted thiazolo [5,4-d]thiazoles are limited in number, laborious and require harsh reaction conditions. A popular method for the preparation of diarylsubstituted thiazolo [5,4-d]thiazole, reported for the first time, 30 is based on the condensation of dithiooxamide with excess aromatic aldehydes (10-12-fold molar excess), which is used for oxidation of the initially formed products. This reaction is carried out in diverse solvents, 10,[31][32][33][34] or without solvent.…”

Diastereoisomeric dinuclear ruthenium complexes of 2,5-di(2-pyridyl)thiazolo[5,4-d]thiazole

“…8 In this way the ligand (5) was prepared from 2-pyridinecarboxaldehyde in 19% yield after recrystallisation, and characterised by mp, mass spectrometry and 1 H NMR. The only previous report 9 of this compound involved a screening of its potential antibacterial activity; no metal complexes have been described.…”