Polycyclic N-Heterocyclic Compounds. Part 63: Improved Synthesis of 5-Amino-1,2-dihydrofuro[2,3-c]isoquinolines via Truce–Smiles Rearrangement and Subsequent Formation to Furo[2,3-c]isoquinoline

Kensuke Okuda; Masahiko Yoshida; Takashi Hirota; Kenji Sasaki

doi:10.1248/cpb.58.363

Regular Articles

Polycyclic N-Heterocyclic Compounds. Part 63: Improved Synthesis of 5-Amino-1,2-dihydrofuro[2,3-c]isoquinolines via Truce–Smiles Rearrangement and Subsequent Formation to Furo[2,3-c]isoquinoline

Kensuke Okuda, Masahiko Yoshida, Takashi Hirota, Kenji Sasaki

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Keywords: Truce–Smiles rearrangement, furo[2,3-c]isoquinoline, furo[2,3-b]pyridine, heterocycle, spiro[cyclopropane-(1,4′)-isoquinoline]

JOURNAL FREE ACCESS

2010 Volume 58 Issue 3 Pages 363-368

DOI https://doi.org/10.1248/cpb.58.363

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Abstract

An improved synthesis of 5-amino-1,2-dihydrofuro[2,3-c]isoquinoline has been achieved using a slight modification of reaction conditions for the Truce–Smiles rearrangement. Acid treatment of the obtained 5-amino-1,2-dihydrofuro[2,3-c]isoquinolines gave unexpected ring-opened spiro ring compounds. The previously unreported parent compound, furo[2,3-c]isoquinoline, was also synthesized.

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