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2005
Isoquinoline derivatives
R 0420
A Convenient Synthesis of 1-Benzyl-1,2,3,4-tetrahydroisoquinolines by Combined
Reaction. — The initial Strecker reaction is performed in the
05- 130 Strecker/Bruylants
presence of sodium hydrogen sulfite yielding α-aminonitriles (IV), accompanied by remarkable amounts of impurities. The impurities are removable by FC or crystallization.
On treatment with i-propyl magnesium chlorides, (IV) undergoes a Bruylants reaction
providing the title compounds (V). Educt (IIc), not described until now, is almost quantitatively obtained by oxidation. This method should be an alternative approach to overcome limitations arising from constructions of tetrahydroisoquinolines using, for example, the Bischler—Napieralski, Pictet—Spengler and Pomeranz—Fritsch reactions.
— (REIMANN*, E.; ETTMAYR, C.; Monatsh. Chem. 135 (2004) 10, 1289-1295;
Inst. Pharm., Zent. Pharmaforsch., Ludwig-Maximilians-Univ., D-81377 Muenchen,
Germany; Eng.) — H. Hoennerscheid
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