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Communication | Regular issue | Vol 55, No. 3, 2001, pp.435-438
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9115
Novel Synthesis of Pyrrolo[2,1-a]isoquinoline Using the Reaction of Isoquinolinium Salts with Active Methylene Compounds

Reiko Fujita,* Noriyuki Watanabe, and Hiroshi Tomisawa

*Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan


2-Alkyl-1-methylthioisoquinolinium salts were easily prepared from 2-alkyl-1(2H)-isoquinolones via 2-alkyl-1(2H)-thioisoquinolones in two steps. Under mild conditions, the reaction of 2-alkyl-l-methylthioisoquin-olinium salts with active methylene compounds in the presence of sodium hydride afforded 2-alkyl-1-(substituted methylene)isoquinolines in good yields. The cyclization of 2-benzylisoquinolines using acetic anhydride produced the pyrrolo[2,1-a]isoquinolines. Further, the reaction of 1-chloro-2-phenacylisoquinolinium salt with active methylene compounds afforded the pyrrolo[2,1-a]isoquinolines in one pot.