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

Improved synthesis for the rodenticides, diphenacoum and brodifacoum

PS van Heerden, BCB Bezuidenhoudt…

Index: Van Heerden, Pieter S.; Bezuidenhoudt, Barend C. B.; Ferreira, Daneel Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 8 p. 1141 - 1146

Full Text: HTML

Citation Number: 24

Abstract

An improved synthesis of the 3-[3-(p-substituted phenyl)-1, 2, 3, 4-tetrahydro-1-napththyl]-4- hydroxycoumarins, diphenacoum and brodifacoum, is described. The process is primarily based on the formation of one of the crucial bonds in the carbon backbone using organocopper methodology, and on the coupling of the 4-hydroxycoumarin moiety to the 3- biphenyl tetralin unit under strongly acidic conditions.

3-(4'-Bromo[1,1'-biphenyl]-4-yl)-1,2,3,4-tetrahydro-1-naphthalenol Structure

3-(4'-Bromo[1,1...

~91%

1-bromo-3-[4'-bromo(1,1'-biphenyl)-4-yl]-1,2,3,4-tetrahydronaphthalene Structure

1-bromo-3-[4'-b...

ethyl 3-(4'-bromo-[1,1'-biphenyl]-4-yl)-4-phenylbutanoate Structure

ethyl 3-(4'-bro...

~84%

3-(4'-bromo[1,1'-biphenyl]-4-yl)-3,4-dihydronaphthalen-1(2H)-one Structure

3-(4'-bromo[1,1...

4,4'-Dibromobiphenyl Structure

4,4'-Dibromobiphenyl

~%

3-(4'-bromo[1,1'-biphenyl]-4-yl)-3,4-dihydronaphthalen-1(2H)-one Structure

3-(4'-bromo[1,1...

4'-Bromo-[1,1'-biphenyl]-4-carboxaldehyde Structure

4'-Bromo-[1,1'-...

~%

3-(4'-bromo[1,1'-biphenyl]-4-yl)-3,4-dihydronaphthalen-1(2H)-one Structure

3-(4'-bromo[1,1...

Ethyl (E)-3-[4-(4-bromophenyl)phenyl]prop-2-enoate Structure

Ethyl (E)-3-[4-...

~%

3-(4'-bromo[1,1'-biphenyl]-4-yl)-3,4-dihydronaphthalen-1(2H)-one Structure

3-(4'-bromo[1,1...

Benzylmagnesium chloride Structure

Benzylmagnesium...

~%

3-(4'-bromo[1,1'-biphenyl]-4-yl)-3,4-dihydronaphthalen-1(2H)-one Structure

3-(4'-bromo[1,1...

4,4'-Dibromobiphenyl Structure

4,4'-Dibromobiphenyl

N,N-Dimethylformamide Structure

N,N-Dimethylfor...

~96%

4'-Bromo-[1,1'-biphenyl]-4-carboxaldehyde Structure

4'-Bromo-[1,1'-...

3-[1,1'-Biphenyl]-4-yl-1,2,3,4-tetrahydro-1-naphthol Structure

3-[1,1'-Bipheny...

~92%

1-bromo-3-(4-phenylphenyl)-1,2,3,4-tetrahydronaphthalene Structure

1-bromo-3-(4-ph...

ethyl 3-([1,1'-biphenyl]-4-yl)-4-phenylbutanoate Structure

ethyl 3-([1,1'-...

~90%

3-[1,1'-biphenyl]-4-yl-3,4-dihydronaphthalen-1(2H)-one Structure

3-[1,1'-bipheny...

3-biphenyl-4-yl-acrylic acid ethyl ester Structure

3-biphenyl-4-yl...

~%

3-[1,1'-biphenyl]-4-yl-3,4-dihydronaphthalen-1(2H)-one Structure

3-[1,1'-bipheny...

Benzylmagnesium chloride Structure

Benzylmagnesium...

~%

3-[1,1'-biphenyl]-4-yl-3,4-dihydronaphthalen-1(2H)-one Structure

3-[1,1'-bipheny...

Synthesis and antitumor activity of 4-hydroxycoumarin deriva...

[Jung, Jae-Chul; Lee, Ji-Ho; Oh, Seikwan; Lee, Jae-Gon; Park, Oee-Sook Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 22 p. 5527 - 5531]

Synthesis and antitumor activity of 4-hydroxycoumarin deriva...

[Jung, Jae-Chul; Lee, Ji-Ho; Oh, Seikwan; Lee, Jae-Gon; Park, Oee-Sook Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 22 p. 5527 - 5531]

Synthesis and antitumor activity of 4-hydroxycoumarin deriva...

[Jung, Jae-Chul; Lee, Ji-Ho; Oh, Seikwan; Lee, Jae-Gon; Park, Oee-Sook Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 22 p. 5527 - 5531]

Synthesis and antitumor activity of 4-hydroxycoumarin deriva...

[Jung, Jae-Chul; Lee, Ji-Ho; Oh, Seikwan; Lee, Jae-Gon; Park, Oee-Sook Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 22 p. 5527 - 5531]

Synthesis and antitumor activity of 4-hydroxycoumarin deriva...

[Jung, Jae-Chul; Lee, Ji-Ho; Oh, Seikwan; Lee, Jae-Gon; Park, Oee-Sook Bioorganic and Medicinal Chemistry Letters, 2004 , vol. 14, # 22 p. 5527 - 5531]