American Chemical Society
jo9b00791_si_003.cif (22.64 kB)

Brønsted-Acid-Catalyzed Synthesis of 3‑Alkoxy and 3‑Sulfamido Indanones via a Tandem Cyclization

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posted on 2019-05-22, 00:00 authored by Ni-Ni Zhou, Si-Si Ning, Xiao-Juan Tong, Ting-Ting Luo, Jin Yang, Lin-Qiang Li, Ming-Jin Fan, De-Suo Yang, Hai-Tao Zhu
Brønsted-acid-catalyzed allylic substitution reactions of the in situ generated 3-hydroxy indanones with alcohols and sulfamides were investigated, which provided a facile route for the synthesis of a large variety of 3-alkoxy and 3-sulfamido indanones. The key intermediates, 3-hydroxy indanones, were obtained through the intramolecular Meyer–Schuster rearrangement of o-propargyl alcohol benzaldehydes. The resulting 3-benzyloxy indanone could be selectively modified by allylic sulfonamidation and reduction reactions.