English (United Kingdom)

https://curated-unify.zendy.io/wp-json/zendy-region/v1/featured_content/oa?rat=en

https://curated-unify.zendy.io/wp-json/zendy-region/v1/highlighted_journal/

Global: Zendy Plus annual

Presents the access of premium content as premium feature

Premium Content

Presents the keyphrase highlighting as premium feature

Keyphrase Highlighting

Presents the summarisation as premium feature

Summarisation

Insights

Presents the pdf analysis as premium feature

PDF Analysis

Presents the zaia usage as premium feature

ZAIA

Global: Zendy Tools annual

Global: Zendy Free Plan

Global: Zendy Tools monthly

Global: Zendy Plus monthly

The synthesis of 4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinolines (16) was achieved via the intramolecular cyclization of N-(arylmethyl)-N-methyl-2-aryl-2-(phenylsulfinyl)acetamides (10) utilizing the Pummerer reaction as key step. Trifuoroacetic anhydride induced cyclization of the sulfoxides 10 at ambient temperature readily provided 4-aryl-2-methyl-4-(phenylsulfanyl)- 1,2,3,4-tetrahydroisoquinolin-3-ones (11) in almost quantitative yield. Subsequent reductive removal of the phenylsulfanyl group from 11 with NaBH4-NiCl2 followed by the reduction of the lactam function of the resulting 4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinolin-3-ones (15) furnished the title products 16 in excellent yields. This conversion offers a total synthesis of (±)- cherylline 16g, an amaryllidaceae alkaloid.

arkivoc

Synthesis of 4-aryl-2-methyl-1,2,3,4-tetrahydroisoquinolines via Pummerer-type cyclization of N-(arylmethyl)-N-methyl-2-aryl-2-(phenylsulfinyl) acetamides