Polycyclic N-heterocyclic compounds. Part 631 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

Polycyclic N-heterocyclic compounds. Part 63¹ 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

Institute for Education and Student Services

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

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.

Original language	English
Pages (from-to)	363-368
Number of pages	6
Journal	Chemical and Pharmaceutical Bulletin
Volume	58
Issue number	3
DOIs	https://doi.org/10.1248/cpb.58.363
Publication status	Published - Mar 2010

Keywords

Furo[2,3-b]pyridine
Furo[2,3-c]isoquinoline
Heterocycle
Spiro[cyclopropane-(1,4′)-isoquinoline]
Truce-smiles rearrangement

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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Polycyclic N-heterocyclic compounds. Part 63¹ 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. / Okuda, Kensuke; Yoshida, Masahiko; Hirota, Takashi; Sasaki, Kenji.

In: Chemical and Pharmaceutical Bulletin, Vol. 58, No. 3, 03.2010, p. 363-368.

Research output: Contribution to journal › Article › peer-review

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