A Modified Bischler-Napieralski Procedure for the Synthesis of 3-Aryl-3,4-dihydroisoquinolines

Robert D. Larsen; Robert A. Reamer; Edward G. Corley; Paul Davis; Edward J.J. Grabowski; Paul J. Reider; Ichiro Shinkai

doi:10.1021/jo00021a014

A Modified Bischler-Napieralski Procedure for the Synthesis of 3-Aryl-3,4-dihydroisoquinolines

Robert D. Larsen, Robert A. Reamer, Edward G. Corley, Paul Davis, Edward J.J. Grabowski, Paul J. Reider, Ichiro Shinkai

Research output: Contribution to journal › Article › peer-review

107 Scopus citations

Abstract

A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl₃. Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields. The method is also highly effective with (2-phenylethyl)amides.

Original language	English (US)
Pages (from-to)	6034-6038
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	56
Issue number	21
DOIs	https://doi.org/10.1021/jo00021a014
State	Published - Oct 1 1991
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00021a014

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title = "A Modified Bischler-Napieralski Procedure for the Synthesis of 3-Aryl-3,4-dihydroisoquinolines",

abstract = "A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3. Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields. The method is also highly effective with (2-phenylethyl)amides.",

author = "Larsen, {Robert D.} and Reamer, {Robert A.} and Corley, {Edward G.} and Paul Davis and Grabowski, {Edward J.J.} and Reider, {Paul J.} and Ichiro Shinkai",

year = "1991",

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doi = "10.1021/jo00021a014",

language = "English (US)",

volume = "56",

pages = "6034--6038",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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T1 - A Modified Bischler-Napieralski Procedure for the Synthesis of 3-Aryl-3,4-dihydroisoquinolines

AU - Larsen, Robert D.

AU - Reamer, Robert A.

AU - Corley, Edward G.

AU - Davis, Paul

AU - Grabowski, Edward J.J.

AU - Reider, Paul J.

AU - Shinkai, Ichiro

PY - 1991/10/1

Y1 - 1991/10/1

N2 - A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3. Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields. The method is also highly effective with (2-phenylethyl)amides.

AB - A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3. Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields. The method is also highly effective with (2-phenylethyl)amides.

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M3 - Article

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 21

ER -

A Modified Bischler-Napieralski Procedure for the Synthesis of 3-Aryl-3,4-dihydroisoquinolines

Abstract

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