Photochemistry of o-Pyrrolylstilbenes and Formation of Spiro-2 H-pyrroles and Their Rearrangement to Dihydroindoles

…, Z Marinic, M Šindler-Kulyk

Index: Basaric, Nikola; Marinic, Zeljko; Sindler-Kulyk, Marija Journal of Organic Chemistry, 2006 , vol. 71, # 25 p. 9382 - 9392

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Citation Number: 26

Abstract

Excited states of stilbenylpyrroles 1a-1c deactivate by two photochemical processes: cis- trans-isomerization and hydrogen transfer of NH to the stilbene double bond. NH-transfer results in the formation of two quinone dimethane intermediates, 10 and 11, and biradicals 12. Intramolecular cyclization of intermediates 10-12 gives rise to polycyclic compounds spiro-2 H-pyrroles 7, pyrroloisoindoles 3, and pyrroloisoquinolines 8. Spiro-2 H-pyrroles 7 ...