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

Journal of Chemical Research

Facile synthesis of 3-(diarylmethylene) isobenzofuranones, 4-(diarylmethyl)-1 (2H)-phthalazinones and diarylmethanes

S Das, R FrÖhlich, A Pramanik

Index: Das, Suven; Froehlich, Roland; Pramanik, Animesh Journal of Chemical Research, 2006 , # 2 p. 84 - 86

Full Text: HTML

Citation Number: 0

Abstract

Reflux of 2, 2-diaryl-1, 3-indanediones in ethyleneglycol with a catalytic amount of triethylamine affords 3-(diaryl-methylene) isobenzofuranones in very good yields. The latter produces 4-diarymethyl-1 (2H)-phthalazinones under reflux in hydrazine hydrate (99%), and diarylmethanes upon stirring in ethylenediamine.

1,2-Ethanediamine Structure

1,2-Ethanediamine

3-(bis(4-chlorophenyl)methylene)isobenzofuran-1(3H)-one Structure

3-(bis(4-chloro...

~85%

N-(2-AMINOETHYL)PHTHALIMIDE Structure

N-(2-AMINOETHYL...

4,4'-ddm Structure

N/A Structure

~%

4,4'-ddm Structure

3-[Bis-(4-methoxyphenyl)-methylen]-phthalid Structure

3-[Bis-(4-metho...

1,2-Ethanediamine Structure

1,2-Ethanediamine

~84%

N-(2-AMINOETHYL)PHTHALIMIDE Structure

N-(2-AMINOETHYL...

Benzene,1,1'-methylenebis[4-methoxy- Structure

Benzene,1,1'-me...

2,2-bis(4-methoxyphenyl)indene-1,3-dione Structure

2,2-bis(4-metho...

~%

Benzene,1,1'-methylenebis[4-methoxy- Structure

Benzene,1,1'-me...

3-[Bis-(3,4-dimethoxy-phenyl)-methylen]-phthalid Structure

3-[Bis-(3,4-dim...

1,2-Ethanediamine Structure

1,2-Ethanediamine

~84%

N-(2-AMINOETHYL)PHTHALIMIDE Structure

N-(2-AMINOETHYL...

Benzene,1,1'-methylenebis[3,4-dimethoxy- Structure

Benzene,1,1'-me...

2,2-di(3,4-dimethoxyphenyl)indane-1,3-dione Structure

2,2-di(3,4-dime...

~%

Benzene,1,1'-methylenebis[3,4-dimethoxy- Structure

Benzene,1,1'-me...

1H-Indene-1,3(2H)-dione,2,2-diphenyl- Structure

1H-Indene-1,3(2...

~84%

3-benzhydrylideneisobenzofuran-1-one Structure

3-benzhydrylide...

3-[Bis-(4-methoxyphenyl)-methylen]-phthalid Structure

3-[Bis-(4-metho...

~92%

4-[bis(4-methoxyphenyl)methyl]-2H-phthalazin-1-one Structure

4-[bis(4-methox...

1,2-Ethanediamine Structure

1,2-Ethanediamine

3-(bis(4-iodophenyl)methylene)isobenzofuran-1(3H)-one Structure

3-(bis(4-iodoph...

~87%

N-(2-AMINOETHYL)PHTHALIMIDE Structure

N-(2-AMINOETHYL...

Benzene,1,1'-methylenebis[4-iodo- Structure

Benzene,1,1'-me...

2,2-bis(4-iodophenyl)-1H-indene-1,3(2H)-dione Structure

2,2-bis(4-iodop...

~%

Benzene,1,1'-methylenebis[4-iodo- Structure

Benzene,1,1'-me...

1,2-Ethanediamine Structure

1,2-Ethanediamine

3-(bis(4-bromophenyl)methylene)isobenzofuran-1(3H)-one Structure

3-(bis(4-bromop...

~87%

N-(2-AMINOETHYL)PHTHALIMIDE Structure

N-(2-AMINOETHYL...

Benzene, 1,1-methylenebis[4-bromo- Structure

Benzene, 1,1-me...

2,2-bis(4-bromophenyl)-1H-indene-1,3(2H)-dione Structure

2,2-bis(4-bromo...

~%

Benzene, 1,1-methylenebis[4-bromo- Structure

Benzene, 1,1-me...

1,2-Ethanediamine Structure

1,2-Ethanediamine

N/A Structure

~80%

N-(2-AMINOETHYL)PHTHALIMIDE Structure

N-(2-AMINOETHYL...

Bis(4-fluorophenyl)methane Structure

Bis(4-fluorophe...

N/A Structure

~%

Bis(4-fluorophenyl)methane Structure

Bis(4-fluorophe...

3-[Bis-(4-methoxyphenyl)-methylen]-phthalid Structure

3-[Bis-(4-metho...

1,2-Ethanediamine Structure

1,2-Ethanediamine

~0%

N-(2-AMINOETHYL)PHTHALIMIDE Structure

N-(2-AMINOETHYL...

Benzene,1,1'-methylenebis[4-methoxy- Structure

Benzene,1,1'-me...

3-[Bis-(3,4-dimethoxy-phenyl)-methylen]-phthalid Structure

3-[Bis-(3,4-dim...

1,2-Ethanediamine Structure

1,2-Ethanediamine

~0%

N-(2-AMINOETHYL)PHTHALIMIDE Structure

N-(2-AMINOETHYL...

Benzene,1,1'-methylenebis[3,4-dimethoxy- Structure

Benzene,1,1'-me...

1,2-Ethanediamine Structure

1,2-Ethanediamine

3-(bis(4-bromophenyl)methylene)isobenzofuran-1(3H)-one Structure

3-(bis(4-bromop...

~0%

N-(2-AMINOETHYL)PHTHALIMIDE Structure

N-(2-AMINOETHYL...

Benzene, 1,1-methylenebis[4-bromo- Structure

Benzene, 1,1-me...

1,2-Ethanediamine Structure

1,2-Ethanediamine

3-(bis(4-chlorophenyl)methylene)isobenzofuran-1(3H)-one Structure

3-(bis(4-chloro...

~0%

N-(2-AMINOETHYL)PHTHALIMIDE Structure

N-(2-AMINOETHYL...

4,4'-ddm Structure

1,2-Ethanediamine Structure

1,2-Ethanediamine

3-(bis(4-iodophenyl)methylene)isobenzofuran-1(3H)-one Structure

3-(bis(4-iodoph...

~0%

N-(2-AMINOETHYL)PHTHALIMIDE Structure

N-(2-AMINOETHYL...

Benzene,1,1'-methylenebis[4-iodo- Structure

Benzene,1,1'-me...

1(3H)-Isobenzofuranone, 3-[bis(3-chloro-4-methoxyphenyl)methylene] Structure

1(3H)-Isobenzof...

1,2-Ethanediamine Structure

1,2-Ethanediamine

~0%

N-(2-AMINOETHYL)PHTHALIMIDE Structure

N-(2-AMINOETHYL...

bis-(3-chloro-4-methoxy-phenyl)-methane Structure

bis-(3-chloro-4...

3-benzhydrylideneisobenzofuran-1-one Structure

3-benzhydrylide...

1,2-Ethanediamine Structure

1,2-Ethanediamine

~0%

N-(2-AMINOETHYL)PHTHALIMIDE Structure

N-(2-AMINOETHYL...

Diphenylmethane Structure

Diphenylmethane

1,2-Ethanediamine Structure

1,2-Ethanediamine

3-(di-p-tolylmethylene)isobenzofuran-1(3H)-one Structure

3-(di-p-tolylme...

~0%

N-(2-AMINOETHYL)PHTHALIMIDE Structure

N-(2-AMINOETHYL...

Benzene,1-methyl-4-[(4-methylphenyl)methyl]- Structure

Benzene,1-methy...

1,2-Ethanediamine Structure

1,2-Ethanediamine

N/A Structure

~0%

N-(2-AMINOETHYL)PHTHALIMIDE Structure

N-(2-AMINOETHYL...

Bis(4-fluorophenyl)methane Structure

Bis(4-fluorophe...

Reduction of Carbonyl to Methylene: Organosilane-Ga (OTf) 3 ...

[Surya Prakash; Do, Clement; Mathew, Thomas; Olah, George A. Catalysis Letters, 2011 , vol. 141, # 4 p. 507 - 511]

Facile One??Pot Palladium??Catalyzed Sequential Coupling to ...

[Wang, Xing; Liu, Lian-Hua; Shi, Jin-Hua; Peng, Ji; Tu, Hai-Yang; Zhang, Ai-Dong European Journal of Organic Chemistry, 2013 , # 30 p. 6870 - 6877]

Selective preparation of 4, 4′-dichlorodiphenylmethane over ...

[Kale; Singh Journal of Molecular Catalysis A: Chemical, 2002 , vol. 184, # 1-2 p. 399 - 411]

New Compounds. p, p Dichlorobenzophenone Hydrazone

[Grummitt; Jenkins Journal of the American Chemical Society, 1946 , vol. 68, p. 914]

Preparation of dihalobenzophenones by oxidation under phase-...

[Halpern, Marc; Lysenko, Zenon Journal of Organic Chemistry, 1989 , vol. 54, # 5 p. 1201 - 1203]