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Synthesis and reactions of 1-aryl-2-nitropyrroles. Structural and conformational study of ethyl N-[2′-[1′-(2-nitropyrrolyl)]phenyl]-N-toluene-4-sulfonamide glycinate
Nitration of 1-aryl(or 1-benzyl)pyrroles 1, 2 and 7 has provided the corresponding 2- and 3-nitropyrroles 3 and 5, 4 and 6, and 8 and 9 in a 1:2 ratio. Reductive cyclisation of 3 and 8, gave pyrrolo[1,2-a]quinazolines 11 and 12, and pyrrolo[1,2-b][2.4]benzodiazepine 13, respectively. A conformational study of 5 in the solid and liquid state using X-ray diffraction analysis, molecular dynamics calculations and NMR spectroscopy, is described.