It goes without saying that the development of environmentally friendly and sustainable reaction media instead of the use of volatile organic solvents and corrosive and / or expensive catalysts in the new millennium will continue to attract great attention from the scientific community in order to meet the challenges of protecting mankind and the environment while maintaining commercial viability. To address the shortcomings of already existing environmentally harmful and economically expensive synthesis protocols for the synthesis of various dipyrromethanes (DPMs) and calix Pyrroles (C4Ps) there is a pressing need to synthesize these valuable supramolecular receptors under green conditions. Therefore, we report here for the first time on a simple but very effective green protocol for the construction of diverse functionalized DPMs and C4Ps in respectable yields without the involvement of an additional catalyst or a conventional organic solvent. A number of deep eutectic mixtures were tested in our study, but a low-melting mixture of N, N’-dimethylurea (DMU) and L – (+) – tartaric acid (TA) in a ratio of 7: 3 at 70 oC was found to be the best choice . Interestingly, this method also works for the large-scale synthesis of these systems without significantly reducing the yields, which seems remarkable from an industrial point of view.