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

Reactions of 1, 2-naphthoquinones with allyltrialkyltins

…, Y Naruta, O Soga, K Maruyama

Index: Takuwa, Akio; Naruta, Yoshinori; Soga, Osamu; Maruyama, Kazuhiro Journal of Organic Chemistry, 1984 , vol. 49, # 11 p. 1857 - 1864

Full Text: HTML

Citation Number: 34

Abstract

BF3-mediated allylation of 1, 2-naphthoquinone and its 3-substituted derivativea with allyl- ,(2-methyl-2-propenyl)-, trans-2-butenyl-, and (3-methyl-2-buteny1) trialkyltin afforded selectively the corresponding 4-allyl-1, 2-naphthalenediols, which were isolated as diacetate or quinone. In the reactions with trans-2-butenyltributyltin, the regioisomer ratio of the a-vs. yadduct depends on the nature of substituents in position 3 of quinones. The ...

4-allyl-3-methoxy-1,2-naphthalenediol Structure

4-allyl-3-metho...

~%

3-methoxy-4-prop-2-enylnaphthalene-1,2-dione Structure

3-methoxy-4-pro...

2-hydroxy-3-methoxy-2-prop-2-enylnaphthalen-1-one Structure

2-hydroxy-3-met...

~%

3-methoxy-4-prop-2-enylnaphthalene-1,2-dione Structure

3-methoxy-4-pro...

2-hydroxy-3-ethoxynaphthalene Structure

2-hydroxy-3-eth...

~%

3-ethoxy-4-prop-2-enylnaphthalene-1,2-dione Structure

3-ethoxy-4-prop...

3-ethoxynaphthalene-1,2-dione Structure

3-ethoxynaphtha...

~%

3-ethoxy-4-prop-2-enylnaphthalene-1,2-dione Structure

3-ethoxy-4-prop...

3-ethoxy-2-hydroxy-2-prop-2-enylnaphthalen-1-one Structure

3-ethoxy-2-hydr...

~%

3-ethoxy-4-prop-2-enylnaphthalene-1,2-dione Structure

3-ethoxy-4-prop...

3-acetylnaphthalene-1,2-dione Structure

3-acetylnaphtha...

N/A Structure

~80%

3-acetyl-2-but-3-en-2-yl-2-hydroxynaphthalen-1-one Structure

3-acetyl-2-but-...

3-acetyl-4-but-3-en-2-yl-2-hydroxy-4H-naphthalen-1-one Structure

3-acetyl-4-but-...

Ethanone, 1-(3,4-dihydroxy-2-naphthalenyl)- (9CI) Structure

Ethanone, 1-(3,...

~%

3-acetyl-4-but-3-en-2-yl-2-hydroxy-4H-naphthalen-1-one Structure

3-acetyl-4-but-...

3-acetylnaphthalene-1,2-dione Structure

3-acetylnaphtha...

N/A Structure

~10%

3-acetyl-2-but-3-en-2-yl-2-hydroxynaphthalen-1-one Structure

3-acetyl-2-but-...

3-acetyl-4-but-3-en-2-yl-2-hydroxy-4H-naphthalen-1-one Structure

3-acetyl-4-but-...

Ethanone, 1-(3,4-dihydroxy-2-naphthalenyl)- (9CI) Structure

Ethanone, 1-(3,...

~%

3-acetyl-2-but-3-en-2-yl-2-hydroxynaphthalen-1-one Structure

3-acetyl-2-but-...

3-methoxy-1,2-naphthoquinone Structure

3-methoxy-1,2-n...

trimethyl(prop-2-enyl)stannane Structure

trimethyl(prop-...

~91%

2-hydroxy-3-methoxy-2-prop-2-enylnaphthalen-1-one Structure

2-hydroxy-3-met...

trimethyl(prop-2-enyl)stannane Structure

trimethyl(prop-...

3-ethoxynaphthalene-1,2-dione Structure

3-ethoxynaphtha...

~88%

3-ethoxy-2-hydroxy-2-prop-2-enylnaphthalen-1-one Structure

3-ethoxy-2-hydr...

2-hydroxy-3-ethoxynaphthalene Structure

2-hydroxy-3-eth...

~%

3-ethoxy-2-hydroxy-2-prop-2-enylnaphthalen-1-one Structure

3-ethoxy-2-hydr...

1,2-Naphthalenedione,3-nitro- Structure

1,2-Naphthalene...

prenyltributyltin Structure

prenyltributyltin

~45%

2-hydroxy-2-(3-methylbut-2-enyl)-3-nitronaphthalen-1-one Structure

2-hydroxy-2-(3-...

1,2-Naphthalenedione,3-nitro- Structure

1,2-Naphthalene...

trimethyl(3-methylbut-2-enyl)stannane Structure

trimethyl(3-met...

~45%

2-hydroxy-2-(3-methylbut-2-enyl)-3-nitronaphthalen-1-one Structure

2-hydroxy-2-(3-...

1,2-Naphthalenedione,3-nitro- Structure

1,2-Naphthalene...

~%

acetic acid,3-methoxy-4-prop-2-enylnaphthalene-1,2-diol Structure

acetic acid,3-m...

Ethanoic anhydride Structure

Ethanoic anhydride

2-hydroxy-3-methoxy-2-prop-2-enylnaphthalen-1-one Structure

2-hydroxy-3-met...

2-hydroxy-2-(3-methylbut-2-enyl)-3-nitronaphthalen-1-one Structure

2-hydroxy-2-(3-...

~%

acetic acid,3-methoxy-4-prop-2-enylnaphthalene-1,2-diol Structure

acetic acid,3-m...

Detail

Ethanone, 1-(3,4-dihydroxy-2-naphthalenyl)- (9CI) Structure

Ethanone, 1-(3,...

~%

acetic acid,4-but-2-enyl-3-ethylnaphthalene-1,2-diol Structure

acetic acid,4-b...

but-2-enyl-[(tri-n-butyl)]-stannane Structure

but-2-enyl-[(tr...

3-ethylnaphthalene-1,2-dione Structure

3-ethylnaphthal...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

acetic acid,4-but-2-enyl-3-ethylnaphthalene-1,2-diol Structure

acetic acid,4-b...

3-Hydroxy-2-naphthalenecarboxylic acid ethyl ester Structure

3-Hydroxy-2-nap...

~%

ethyl 3,4-dioxonaphthalene-2-carboxylate Structure

ethyl 3,4-dioxo...

3-chloronaphthalene-1,2-dione Structure

3-chloronaphtha...

but-2-enyl-[(tri-n-butyl)]-stannane Structure

but-2-enyl-[(tr...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

acetic acid,4-but-2-enyl-3-chloronaphthalene-1,2-diol Structure

acetic acid,4-b...

Detail

3-bromonaphthalene-1,2-dione Structure

3-bromonaphthal...

but-2-enyl-[(tri-n-butyl)]-stannane Structure

but-2-enyl-[(tr...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

acetic acid,3-bromo-4-but-2-enylnaphthalene-1,2-diol Structure

acetic acid,3-b...

Detail

3-bromonaphthalene-1,2-dione Structure

3-bromonaphthal...

but-2-enyl-[(tri-n-butyl)]-stannane Structure

but-2-enyl-[(tr...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

acetic acid,3-bromo-4-but-2-enylnaphthalene-1,2-diol Structure

acetic acid,3-b...

Detail

Ethanone, 1-(3,4-dihydroxy-2-naphthalenyl)- (9CI) Structure

Ethanone, 1-(3,...

~%

[3-acetyl-2-acetyloxy-4-(3-methylbut-2-enyl)naphthalen-1-yl] acetate Structure

[3-acetyl-2-ace...

3-acetylnaphthalene-1,2-dione Structure

3-acetylnaphtha...

~%

[3-acetyl-2-acetyloxy-4-(3-methylbut-2-enyl)naphthalen-1-yl] acetate Structure

[3-acetyl-2-ace...

4-(2-methyl-2-propenyl)-1,2-naphthalenediol Structure

4-(2-methyl-2-p...

~%

4-(2-methylprop-2-enyl)naphthalene-1,2-dione Structure

4-(2-methylprop...

1,2-NAPHTHOQUINONE Structure

1,2-NAPHTHOQUINONE

~%

4-(2-methylprop-2-enyl)naphthalene-1,2-dione Structure

4-(2-methylprop...

2-hydroxy-3-ethoxynaphthalene Structure

2-hydroxy-3-eth...

~%

3-ethoxynaphthalene-1,2-dione Structure

3-ethoxynaphtha...

1,2-Naphthalenedione,3-nitro- Structure

1,2-Naphthalene...

trimethyl(prop-2-enyl)stannane Structure

trimethyl(prop-...

~82%

2-hydroxy-3-nitro-2-prop-2-enylnaphthalen-1-one Structure

2-hydroxy-3-nit...

2-hydroxy-3-nitro-4-prop-2-enyl-4H-naphthalen-1-one Structure

2-hydroxy-3-nit...

1,2-Naphthalenedione,3-nitro- Structure

1,2-Naphthalene...

trimethyl(prop-2-enyl)stannane Structure

trimethyl(prop-...

~19%

2-hydroxy-3-nitro-2-prop-2-enylnaphthalen-1-one Structure

2-hydroxy-3-nit...

2-hydroxy-3-nitro-4-prop-2-enyl-4H-naphthalen-1-one Structure

2-hydroxy-3-nit...

3-methylnaphthalene-1,2-dione Structure

3-methylnaphtha...

but-2-enyl-[(tri-n-butyl)]-stannane Structure

but-2-enyl-[(tr...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

acetic acid,4-but-2-enyl-3-methylnaphthalene-1,2-diol Structure

acetic acid,4-b...

Detail

3-methylnaphthalene-1,2-dione Structure

3-methylnaphtha...

but-2-enyl-[(tri-n-butyl)]-stannane Structure

but-2-enyl-[(tr...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

acetic acid,4-but-2-enyl-3-methylnaphthalene-1,2-diol Structure

acetic acid,4-b...

Detail

1,2-NAPHTHOQUINONE Structure

1,2-NAPHTHOQUINONE

~%

acetic acid,4-(3-methylbut-2-enyl)naphthalene-1,2-diol Structure

acetic acid,4-(...

3-acetylnaphthalene-1,2-dione Structure

3-acetylnaphtha...

trimethyl(prop-2-enyl)stannane Structure

trimethyl(prop-...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

(3-nitro-1-oxo-2-prop-2-enylnaphthalen-2-yl) acetate Structure

(3-nitro-1-oxo-...

Detail

3-propanoylnaphthalene-1,2-dione Structure

3-propanoylnaph...

trimethyl(prop-2-enyl)stannane Structure

trimethyl(prop-...

~%

2-hydroxy-3-propanoyl-2-prop-2-enylnaphthalen-1-one Structure

2-hydroxy-3-pro...

2-hydroxy-3-propanoyl-4-prop-2-enyl-4H-naphthalen-1-one Structure

2-hydroxy-3-pro...

1-(3,4-dihydroxynaphthalen-2-yl)propan-1-one Structure

1-(3,4-dihydrox...

~%

2-hydroxy-3-propanoyl-4-prop-2-enyl-4H-naphthalen-1-one Structure

2-hydroxy-3-pro...

3-chloronaphthalene-1,2-dione Structure

3-chloronaphtha...

~%

acetic acid,3-chloro-4-(3-methylbut-2-enyl)naphthalene-1,2-diol Structure

acetic acid,3-c...

prenyltributyltin Structure

prenyltributyltin

~%

acetic acid,3-chloro-4-(3-methylbut-2-enyl)naphthalene-1,2-diol Structure

acetic acid,3-c...

Ethanone, 1-(3,4-dihydroxy-2-naphthalenyl)- (9CI) Structure

Ethanone, 1-(3,...

~%

(3-acetyl-2-acetyloxy-4-prop-2-enylnaphthalen-1-yl) acetate Structure

(3-acetyl-2-ace...

3-acetylnaphthalene-1,2-dione Structure

3-acetylnaphtha...

~%

(3-acetyl-2-acetyloxy-4-prop-2-enylnaphthalen-1-yl) acetate Structure

(3-acetyl-2-ace...

3-propanoylnaphthalene-1,2-dione Structure

3-propanoylnaph...

trimethyl(prop-2-enyl)stannane Structure

trimethyl(prop-...

~%

2-hydroxy-3-propanoyl-2-prop-2-enylnaphthalen-1-one Structure

2-hydroxy-3-pro...

2-hydroxy-3-propanoyl-4-prop-2-enyl-4H-naphthalen-1-one Structure

2-hydroxy-3-pro...

1-(3,4-dihydroxynaphthalen-2-yl)propan-1-one Structure

1-(3,4-dihydrox...

~%

2-hydroxy-3-propanoyl-2-prop-2-enylnaphthalen-1-one Structure

2-hydroxy-3-pro...

but-2-enyl-[(tri-n-butyl)]-stannane Structure

but-2-enyl-[(tr...

Ethanoic anhydride Structure

Ethanoic anhydride

1,2-NAPHTHOQUINONE Structure

1,2-NAPHTHOQUINONE

~%

acetic acid,4-but-2-enylnaphthalene-1,2-diol Structure

acetic acid,4-b...

Detail

3-methoxy-1,2-naphthoquinone Structure

3-methoxy-1,2-n...

~%

3-methoxy-4-(3-methylbut-2-enyl)naphthalene-1,2-dione Structure

3-methoxy-4-(3-...

prenyltributyltin Structure

prenyltributyltin

~%

3-methoxy-4-(3-methylbut-2-enyl)naphthalene-1,2-dione Structure

3-methoxy-4-(3-...

2-hydroxy-5,6-benzo-2-(1-methyl-2-propenyl)-4-methoxycyclohex-3-en-1-one Structure

2-hydroxy-5,6-b...

~88%

4-but-2-enylnaphthalene-1,2-dione Structure

4-but-2-enylnap...

4-methoxynaphthalene-1,2-dione Structure

4-methoxynaphth...

~%

4-but-2-enylnaphthalene-1,2-dione Structure

4-but-2-enylnap...

1-(3,4-dihydroxynaphthalen-2-yl)propan-1-one Structure

1-(3,4-dihydrox...

~%

(2-acetyloxy-3-propanoyl-4-prop-2-enylnaphthalen-1-yl) acetate Structure

(2-acetyloxy-3-...

3-propanoylnaphthalene-1,2-dione Structure

3-propanoylnaph...

~%

(2-acetyloxy-3-propanoyl-4-prop-2-enylnaphthalen-1-yl) acetate Structure

(2-acetyloxy-3-...

3-chloronaphthalene-1,2-dione Structure

3-chloronaphtha...

~%

3-chloro-4-prop-2-enylnaphthalene-1,2-dione Structure

3-chloro-4-prop...

but-2-enyl-[(tri-n-butyl)]-stannane Structure

but-2-enyl-[(tr...

Ethanoic anhydride Structure

Ethanoic anhydride

1,2-NAPHTHOQUINONE Structure

1,2-NAPHTHOQUINONE

~%

acetic acid,4-but-2-enylnaphthalene-1,2-diol Structure

acetic acid,4-b...

Detail

3-acetylnaphthalene-1,2-dione Structure

3-acetylnaphtha...

but-2-enyl-[(tri-n-butyl)]-stannane Structure

but-2-enyl-[(tr...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

(3-acetyl-2-acetyloxy-4-but-2-enylnaphthalen-1-yl) acetate Structure

(3-acetyl-2-ace...

Detail

3-chloro-4-(2-methyl-2-propenyl)-1,2-naphthalenediol Structure

3-chloro-4-(2-m...

~%

3-chloro-4-(2-methylprop-2-enyl)naphthalene-1,2-dione Structure

3-chloro-4-(2-m...

3-methylnaphthalene-1,2-dione Structure

3-methylnaphtha...

~%

3-methyl-4-prop-2-enylnaphthalene-1,2-dione Structure

3-methyl-4-prop...

3-propanoylnaphthalene-1,2-dione Structure

3-propanoylnaph...

but-2-enyl-[(tri-n-butyl)]-stannane Structure

but-2-enyl-[(tr...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

(2-acetyloxy-4-but-2-enyl-3-propanoylnaphthalen-1-yl) acetate Structure

(2-acetyloxy-4-...

Detail

3-chloronaphthalene-1,2-dione Structure

3-chloronaphtha...

but-2-enyl-[(tri-n-butyl)]-stannane Structure

but-2-enyl-[(tr...

Ethanoic anhydride Structure

Ethanoic anhydride

~%

acetic acid,4-but-2-enyl-3-chloronaphthalene-1,2-diol Structure

acetic acid,4-b...

Detail