7471-63-8Relevant articles and documents
Hydrogen-bonded cyclic dimers at large compression: The case of 1h-pyrrolo[3,2-h]quinoline and 2-(2′-pyridyl)pyrrole
Chumak, Taisiia,Kurzyd?owski, Dominik,Listkowski, Arkadiusz,Rogo?a, Jakub
supporting information, (2021/07/10)
1H-pyrrolo[3,2-h]qinoline (PQ) and 2-(2′-pyridyl)pyrrole (PP) are important systems in the study of proton-transfer reactions. These molecules possess hydrogen bond donor (pyrrole) and acceptor (pyridine) groups, which leads to the formation of cyclic dimers in their crystals. Herein, we present a joint experimental (Raman scattering) and computational (DFT modelling) study on the high-pressure behaviour of PQ and PP molecular crystals. Our results indicate that compression up to 10 GPa (100 kbar) leads to considerable strengthening of the intermolecular hydrogen bond within the cyclic dimers. However, the intramolecular N–H···N interaction is either weakly affected by pressure, as witnessed in PQ, or weakened due to compression-induced distortions of the molecule, as was found for PP. Therefore, we propose that the compression of these systems should facilitate double proton transfer within the cyclic dimers of PQ and PP, while intramolecular transfer should either remain unaffected (for PQ) or weakened (for PP).
Selective ortho methylation of nitroheteroaryls by vicarious nucleophilic substitution
Achmatowicz, Michal,Thiel, Oliver R.,Gorins, Gilles,Goldstein, Corinne,Affouard, Caroline,Jensen, Randy,Larsen, Robert D.
, p. 6793 - 6799 (2008/12/22)
(Chemical Equation Presented) An efficient and scalable three-step one-pot approach to 6-methyl-5-nitroisoquinoline (1) from inexpensive 5-nitroisoquinoline, utilizing the vicarious nucleophilic substitution (VNS) as a key step, is described. The optimized reaction conditions can be applied to a limited number of other aromatic and heteroaromatic nitro compounds. Attempts to understand the observed selectivity in the VNS step led to the discovery of two new reaction pathways under VNS conditions, one leading to an isoxazole and the other resulting in the formal cyclopropanation of an aromatic nitro compound.