4.3 Article

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

Journal

CHEMICAL & PHARMACEUTICAL BULLETIN
Volume 58, Issue 3, Pages 363-368

Publisher

PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.58.363

Keywords

Truce-Smiles rearrangement; furo[2,3-c]isoquinoline; furo[2,3-c]isoquinoline; furo[2,3-b]pyridine; heterocycle; spiro[cyclopropane-(1-4 ')-isoquinoline]

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An improved synthesis of 5-amino-1,2-dihydrofuro[2,3-c]isoquinoline has been achieved using a slight niodification 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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