ChemInform Abstract: STUDIES ON THE SYNTHESES OF HETEROCYCLIC COMPOUNDS PART 591, TOTAL SYNTHESIS OF (+‐)‐CHERYLLINE AND CORGOINE THROUGH QUINONOID INTERMEDIATES

Kametani, Tetsuji; Takahashi, Keiichi; Loc, Chu Van

doi:10.1002/chin.197519422

Cited by 1 publication

(1 citation statement)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The importance of these heterocyclic compounds has generated a considerable number of synthetic approaches. Hence, the formation of the nitrogen-containing ring of 4-substituted 1,2,3,4-tetrahydroisoquinolines has been achieved with several reactions such as Bischler-Napieralski [ 24 , 25 , 26 ], intramolecular Horner [ 27 ], Friedel-Crafts [ 21 , 27 , 28 , 29 , 30 , 31 , 32 ] Pictet-Spengler [ 33 ], and oxazoline-driven chemistry [ 34 ], among others [ 25 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 ]. Most of the reported methods for the synthesis of these compounds are either multistep or low yielding.…”

Section: Introductionmentioning

confidence: 99%

Silica-Supported Polyphosphoric Acid in the Synthesis of 4-Substituted Tetrahydroisoquinoline Derivatives

Manolov¹,

Nikolova²,

Ivanov³

2013

Molecules

View full text Add to dashboard Cite

We report herein an application of an α-amidoalkylation reaction, as an alternative efficient synthesis of 4-aryl- and 4-methyl-1,2,3,4-tetrahydroisoquinoline derivatives. The amides required for this purpose would result from reaction of aminoacetaldehyde dimethylacetal with different substituted benzenes in polyphosphoric acid, followed by acylation of the obtained amines with different acid chlorides or sulfochlorides. We compared the cyclisation step using conventional (milieu of acetic-trifluoracetic acid = 4:1) and solid supported reagents (SiO2/PPA), as recovered, regenerated and reused without loss of its activity catalyst. We found that in comparison to conventional methods, the yields of the reaction are greater and the reaction time is shorter.

show abstract

Section: Introductionmentioning

confidence: 99%

Silica-Supported Polyphosphoric Acid in the Synthesis of 4-Substituted Tetrahydroisoquinoline Derivatives

Manolov¹,

Nikolova²,

Ivanov³

2013

Molecules

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: STUDIES ON THE SYNTHESES OF HETEROCYCLIC COMPOUNDS PART 591, TOTAL SYNTHESIS OF (+‐)‐CHERYLLINE AND CORGOINE THROUGH QUINONOID INTERMEDIATES

Abstract: Das durch Kondensation des Bromids (I) mit dem Amin (II) erhaltene tertiäre Amin (III) cyclisiert in Gegenwart von Säuren zu (i)‐Cheryllin (IV).

Cited by 1 publication

References 1 publication

Silica-Supported Polyphosphoric Acid in the Synthesis of 4-Substituted Tetrahydroisoquinoline Derivatives

Silica-Supported Polyphosphoric Acid in the Synthesis of 4-Substituted Tetrahydroisoquinoline Derivatives

Contact Info

Product

Resources

About