Add time:08/20/2019         Source:sciencedirect.com

The Lewis acid-catalyzed Diels–Alder reactions of suitably substituted imidazole-2-thiones with dienes were studied. It was found that the electron density of the imidazole core influenced the reaction, since electron withdrawing groups led to the novel spiro-derivatives 2 whereas electron donating groups gave rise to the sulfur substituted imidazole derivatives 6. The reaction conditions were optimized and full assignment of all 1H and 13C NMR chemical shifts has been unambiguously achieved. In silico evaluation of the cycloadducts by means of molecular modeling in three different proteins and calculation of ADME-Tox properties was performed.

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