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Synthesis 1997; 1997(6): 677-680
DOI: 10.1055/s-1997-1402
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A Convenient Synthetic Route to Derivatives of 1,2,3,4-Tetrahydroisoquinoline-1-carboxylic Acid

Alexander F. Khlebnikov1 , Tat'yana Yu. Nikiforova, Mikhail S. Novikov, Rafael R. Kostikov2
  • 1Department of Chemistry, St. Petersburg State University, Universitetskii pr. 2, Petrodvorets, 198904 St. Petersburg, Russia, Fax +7(812)4286939; E-mail: alex@khleb.chem.spb.su
  • 2Department of Chemistry, St. Petersburg State University, Universitetskii pr. 2, Petrodvorets, 198904 St. Petersburg, Russia, Fax +7(812)4286939
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Publication Date:
31 December 2000 (online)

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Alkyl esters and amides of 1,3,3-trisubstituted 1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid as well as 1,2,3,4-tetrahydro-1-(4,5-dihydroimidazol-2-yl)- and 1,2,3,4-tetrahydro-1-(1,4,5,6-tetrahydropyrimidin-2-yl)-1,3,3-trimethylisoquinolines are readily obtained in two steps by the reaction of 3,4-dihydroisoquinolines with dichlorocarbene followed by ring opening of the resulting gem-dichloroaziridine by oxygen and nitrogen nucleophiles.

alkyl 1,2,3,4-tetrahydroisoquiniline-1-carboxylates - alkyl 1,2,3,4-tetrahydroisoquiniline-1-carboxamides - alkyl 1,2,3,4-tetrahydroisoquiniline-1-carboxamidines - gem-dichloroaziridines