e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

A Unified Synthesis of Bifunctional 4??Substituted??1, 2, 3, 4??tetrahydroisoquinoline Derivatives

M Carmen Bernabeu, J Luis Díaz…

Index: Bernabeu, M. Carmen; Diaz, Jose Luis; Jimenez, Oscar; Lavilla, Rodolfo Synthetic Communications, 2004 , vol. 34, # 1 p. 137 - 149

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Citation Number: 3

Abstract

Abstract Starting from a single, commercially available bromoisoquinoline, convenient (multigram) syntheses of 4??substituted??1, 2, 3, 4??tetrahydroisoquinoline derivatives have been developed. The compounds thus prepared show suitable substitution patterns for further derivatization and constitute a new family of compounds of potential pharmacological interest.

4-Bromoisoquinoline Structure

4-Bromoisoquinoline

~97%

Isoquinolin-4-amine Structure

Isoquinolin-4-amine

Methyl isoquinoline-4-carboxylate Structure

Methyl isoquino...

~85%

Methyl 1,2,3,4-tetrahydroisoquinoline-4-carboxylate Structure

Methyl 1,2,3,4-...

N/A Structure

~70%

N-(1,2,3,4-tetrahydroisoquinolin-4-yl)acetamide Structure

N-(1,2,3,4-tetr...

4-Bromoisoquinoline Structure

4-Bromoisoquinoline

~%

N-(1,2,3,4-tetrahydroisoquinolin-4-yl)acetamide Structure

N-(1,2,3,4-tetr...

Isoquinolin-4-amine Structure

Isoquinolin-4-amine

~%

N-(1,2,3,4-tetrahydroisoquinolin-4-yl)acetamide Structure

N-(1,2,3,4-tetr...

4-Bromoisoquinoline Structure

4-Bromoisoquinoline

Copper cyanide Structure

~79%

4-Isoquinolinecarbonitrile Structure

4-Isoquinolinec...

Methanol Structure

4-Isoquinolinecarbonitrile Structure

4-Isoquinolinec...

~68%

Methyl isoquinoline-4-carboxylate Structure

Methyl isoquino...

4-acetoxyisoquinoline Structure

4-acetoxyisoqui...

~69%

1,2,3,4-Tetrahydro-isoquinoline-4-ol Structure

1,2,3,4-Tetrahy...

4-Bromoisoquinoline Structure

4-Bromoisoquinoline

~%

1,2,3,4-Tetrahydro-isoquinoline-4-ol Structure

1,2,3,4-Tetrahy...

Isoquinolin-4-ol Structure

Isoquinolin-4-ol

~%

1,2,3,4-Tetrahydro-isoquinoline-4-ol Structure

1,2,3,4-Tetrahy...

Methyl 1,2,3,4-tetrahydroisoquinoline-4-carboxylate Structure

Methyl 1,2,3,4-...

~90%

1,2,3,4-Tetrahydro-4-isoquinolinecarboxylic acid Structure

1,2,3,4-Tetrahy...

4-Bromoisoquinoline Structure

4-Bromoisoquinoline

~%

1,2,3,4-Tetrahydro-4-isoquinolinecarboxylic acid Structure

1,2,3,4-Tetrahy...

4-Isoquinolinecarbonitrile Structure

4-Isoquinolinec...

~%

1,2,3,4-Tetrahydro-4-isoquinolinecarboxylic acid Structure

1,2,3,4-Tetrahy...

Methyl isoquinoline-4-carboxylate Structure

Methyl isoquino...

~%

1,2,3,4-Tetrahydro-4-isoquinolinecarboxylic acid Structure

1,2,3,4-Tetrahy...

Isoquinolin-4-amine Structure

Isoquinolin-4-amine

Benzoic anhydride Structure

Benzoic anhydride

~89%

Benzamide, N-4-isoquinolinyl- (9CI) Structure

Benzamide, N-4-...

4-Bromoisoquinoline Structure

4-Bromoisoquinoline

~%

Benzamide, N-4-isoquinolinyl- (9CI) Structure

Benzamide, N-4-...