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

Tetrahedron

The synthesis of three new heterocycles: the pyrido [4, 3 or 3, 4 or 2, 3-c]-1, 5-naphthyridines

T Cailly, F Fabis, R Legay, H Oulyadi, S Rault

Index: Cailly, Thomas; Fabis, Frederic; Legay, Remi; Oulyadi, Hassan; Rault, Sylvain Tetrahedron, 2007 , vol. 63, # 1 p. 71 - 76

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Citation Number: 16

Abstract

Pyrido [4, 3 or 3, 4 or 2, 3-c]-1, 5-naphthyridines were obtained with good yields after chlorodehydroxylation and dehalogenation reactions starting from the parent pyridonaphthyridinones. These pyridonaphthyridinones were synthesized in a two-step procedure using a Suzuki cross-coupling reaction between 2-chloro-3-fluoropyridine and orthocyanopyridylboronic esters followed by a KOH-mediated anionic ring closure.

3-fluoro-2,4'-bipyridine-3'-carbonitrile Structure

3-fluoro-2,4'-b...

~75%

5H-pyrido[3,4-c][1,5]naphthyridin-6-one Structure

5H-pyrido[3,4-c...

3-cyano-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine Structure

3-cyano-4-(4,4,...

~%

5H-pyrido[3,4-c][1,5]naphthyridin-6-one Structure

5H-pyrido[3,4-c...

2-Chloro-3-fluoropyridine Structure

2-Chloro-3-fluo...

~%

5H-pyrido[3,4-c][1,5]naphthyridin-6-one Structure

5H-pyrido[3,4-c...

3-Fluoro-[2,3'-bipyridine]-4-carbonitrile Structure

3-Fluoro-[2,3'-...

~78%

5H-pyrido[4,3-c][1,5]naphthyridin-6-one Structure

5H-pyrido[4,3-c...

4-cyano-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine Structure

4-cyano-3-(4,4,...

~%

5H-pyrido[4,3-c][1,5]naphthyridin-6-one Structure

5H-pyrido[4,3-c...

2-Chloro-3-fluoropyridine Structure

2-Chloro-3-fluo...

~%

5H-pyrido[4,3-c][1,5]naphthyridin-6-one Structure

5H-pyrido[4,3-c...

pyrido[2,3-c]-1,5-naphthyridin-6(5H)-one Structure

pyrido[2,3-c]-1...

~72%

6-chloropyrido[2,3-c][1,5]naphthyridine Structure

6-chloropyrido[...

2-Cyanopyridine-3-boronic acid pinacol ester Structure

2-Cyanopyridine...

~%

6-chloropyrido[2,3-c][1,5]naphthyridine Structure

6-chloropyrido[...

2-Chloro-3-fluoropyridine Structure

2-Chloro-3-fluo...

~%

6-chloropyrido[2,3-c][1,5]naphthyridine Structure

6-chloropyrido[...

3-fluoro-2,3'-bipyridine-2'-carbonitrile Structure

3-fluoro-2,3'-b...

~%

6-chloropyrido[2,3-c][1,5]naphthyridine Structure

6-chloropyrido[...

5H-pyrido[4,3-c][1,5]naphthyridin-6-one Structure

5H-pyrido[4,3-c...

~69%

6-chloropyrido[4,3-c][1,5]naphthyridine Structure

6-chloropyrido[...

4-cyano-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine Structure

4-cyano-3-(4,4,...

~%

6-chloropyrido[4,3-c][1,5]naphthyridine Structure

6-chloropyrido[...

2-Chloro-3-fluoropyridine Structure

2-Chloro-3-fluo...

~%

6-chloropyrido[4,3-c][1,5]naphthyridine Structure

6-chloropyrido[...

3-Fluoro-[2,3'-bipyridine]-4-carbonitrile Structure

3-Fluoro-[2,3'-...

~%

6-chloropyrido[4,3-c][1,5]naphthyridine Structure

6-chloropyrido[...

5H-pyrido[3,4-c][1,5]naphthyridin-6-one Structure

5H-pyrido[3,4-c...

~74%

6-chloropyrido[3,4-c][1,5]naphthyridine Structure

6-chloropyrido[...

3-cyano-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine Structure

3-cyano-4-(4,4,...

~%

6-chloropyrido[3,4-c][1,5]naphthyridine Structure

6-chloropyrido[...

2-Chloro-3-fluoropyridine Structure

2-Chloro-3-fluo...

~%

6-chloropyrido[3,4-c][1,5]naphthyridine Structure

6-chloropyrido[...

3-fluoro-2,4'-bipyridine-3'-carbonitrile Structure

3-fluoro-2,4'-b...

~%

6-chloropyrido[3,4-c][1,5]naphthyridine Structure

6-chloropyrido[...