Tetrahedron

A simplified isoquinoline synthesis

DL Boger, CE Brotherton, MD Kelley

Index: Boger, Dale L.; Brotherton, Christine E.; Kelley, Marshall D. Tetrahedron, 1981 , vol. 37, # 23 p. 3977 - 3980

Full Text: HTML

Citation Number: 33

Abstract

A simple variation of the Pomeranz-Fritsch cyclization provides a short, efficient route to isoquinolines. Treatment of benzylic halides or mesylates 1 with the sodium anion of N-tosyl aminoacetaldehyde dimethyl acetal (2) followed by acid-catalyzed cyclization provides an effective, two-step preparation of isoquinolines 4.

Related Articles:

The design, synthesis, and evaluation of organ-specific iron chelators

[Chantimakorn, Vilai; Nimgirawath, Surachai Australian Journal of Chemistry, 1989 , vol. 42, # 1 p. 209 - 213]

Activation of iodosobenzene by catalytic tetrabutylammonium iodide and its application in the oxidation of some isoquinoline alkaloids

[Huang, Wei-Jan; Singh, Om V.; Chen, Chung-Hsiung; Chiou, Sheng-You; Lee, Shoei-Sheng Helvetica Chimica Acta, 2002 , vol. 85, # 4 p. 1069 - 1078]

Activation of iodosobenzene by catalytic tetrabutylammonium iodide and its application in the oxidation of some isoquinoline alkaloids

[Huang, Wei-Jan; Singh, Om V.; Chen, Chung-Hsiung; Chiou, Sheng-You; Lee, Shoei-Sheng Helvetica Chimica Acta, 2002 , vol. 85, # 4 p. 1069 - 1078]

Activation of iodosobenzene by catalytic tetrabutylammonium iodide and its application in the oxidation of some isoquinoline alkaloids

[Huang, Wei-Jan; Singh, Om V.; Chen, Chung-Hsiung; Chiou, Sheng-You; Lee, Shoei-Sheng Helvetica Chimica Acta, 2002 , vol. 85, # 4 p. 1069 - 1078]

Peter Altenberg and das junge Wien

[Spaeth; Polgar Monatshefte fuer Chemie, 1929 , vol. 51, p. 199]

More Articles...