Synthetic approaches to 2‐substituted 1‐oxo‐ and 3‐oxotetrahydroisoquinolines

Chen‐Yu ‐Y Cheng, Hui‐Bing ‐B Tsai, Mei‐Shan ‐S Lin

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

2‐Substituted homophthalimides 2a‐c were reduced regioselectively with sodium borobydride to carbinol‐lactam intermediates 3a‐c, which were dehydrated, followed by hydrogenation, to give 1‐oxo‐tetrabydroisoquinolines or 3,4‐dihydroisoquinolin‐1(2H)ones 5a‐c. The isomeric 3‐oxo‐tetrahydro‐isoquinolines or 1,4‐dihydroisoquinolin‐3(2H)‐ones 8a‐i were obtained in satisfactory yields via heating 3‐isochromanone (6) with the corresponding amines 7a‐i in the presence of aluminum chloride.

Original languageEnglish
Pages (from-to)73-77
Number of pages5
JournalJournal of Heterocyclic Chemistry
Volume32
Issue number1
DOIs
Publication statusPublished - Jan 1 1995
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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