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

Organic letters

Efficient Synthesis of 1, 5-Disubstituted Carbohydrazones Using K2CO3 As a Carbonyl Donor

…, CT Yang, T Jiang, S Hu, TZ Yang, XL Wang

Index: Wen, Jun; Yang, Chu-Ting; Jiang, Tao; Hu, Sheng; Yang, Tong-Zai; Wang, Xiao-Lin Organic Letters, 2014 , vol. 16, # 9 p. 2398 - 2401

Full Text: HTML

Citation Number: 2

Abstract

A novel reaction that generates 1, 5-disubstituted carbohydrazones via the carbonylation of tosylhydrazones has been developed. For the first time, the inexpensive, readily available, environmentally friendly, and nongaseous potassium carbonate is used as the carbonyl donor for the transformation. The reaction system exhibited tolerance with various functional groups and affords the desired products in good to excellent yields. This reaction is ...

Potassium carbonate Structure

Potassium carbonate

2-chlorobenzaldehyde tosylhydrazone Structure

2-chlorobenzald...

~89%

1,3-bis[(2-chlorophenyl)methylideneamino]urea Structure

1,3-bis[(2-chlo...

2-Chlorobenzaldehyde Structure

2-Chlorobenzaldehyde

~%

1,3-bis[(2-chlorophenyl)methylideneamino]urea Structure

1,3-bis[(2-chlo...

N/A Structure

Potassium carbonate Structure

Potassium carbonate

~85%

1,3-bis(naphthalen-1-ylmethylideneamino)urea Structure

1,3-bis(naphtha...

naphthal Structure

~%

1,3-bis(naphthalen-1-ylmethylideneamino)urea Structure

1,3-bis(naphtha...

4-methyl-N'-[(1E)-(4-methylphenyl)methylidene]benzene-1-sulfonohydrazide Structure

4-methyl-N'-[(1...

Potassium carbonate Structure

Potassium carbonate

~85%

Carbonic dihydrazide,bis[(4-methylphenyl)methylene]- (9CI) Structure

Carbonic dihydr...

p-Tolualdehyde Structure

Potassium carbonate Structure

Potassium carbonate

~73%

Carbonic dihydrazide,bis[(4-methylphenyl)methylene]- (9CI) Structure

Carbonic dihydr...

p-Tolualdehyde Structure

~%

Carbonic dihydrazide,bis[(4-methylphenyl)methylene]- (9CI) Structure

Carbonic dihydr...

Potassium carbonate Structure

Potassium carbonate

4-Methoxybenzaldehyde Structure

4-Methoxybenzal...

~77%

Carbonic dihydrazide,bis[(4-methoxyphenyl)methylene]- (9CI) Structure

Carbonic dihydr...

N-[(4-methoxyphenyl)methylideneamino]-4-methyl-benzenesulfonamide Structure

N-[(4-methoxyph...

Potassium carbonate Structure

Potassium carbonate

~82%

Carbonic dihydrazide,bis[(4-methoxyphenyl)methylene]- (9CI) Structure

Carbonic dihydr...

4-Methoxybenzaldehyde Structure

4-Methoxybenzal...

~%

Carbonic dihydrazide,bis[(4-methoxyphenyl)methylene]- (9CI) Structure

Carbonic dihydr...

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

Potassium carbonate Structure

Potassium carbonate

~85%

1,3-bis[(4-chlorophenyl)methylideneamino]urea Structure

1,3-bis[(4-chlo...

4-Chlorobenzaldehyde Structure

4-Chlorobenzaldehyde

~%

1,3-bis[(4-chlorophenyl)methylideneamino]urea Structure

1,3-bis[(4-chlo...

Benzenesulfonic acid,4-methyl-, 2-[(4-chlorophenyl)methylene]hydrazide Structure

Benzenesulfonic...

Potassium carbonate Structure

Potassium carbonate

~93%

1,3-bis[(4-chlorophenyl)methylideneamino]urea Structure

1,3-bis[(4-chlo...

Benzenesulfonic acid,4-methyl-, 2-[(3-nitrophenyl)methylene]hydrazide Structure

Benzenesulfonic...

Potassium carbonate Structure

Potassium carbonate

~94%

1,3-bis[(3-nitrophenyl)methylideneamino]urea Structure

1,3-bis[(3-nitr...

3-Nitrobenzaldehyde Structure

3-Nitrobenzaldehyde

~%

1,3-bis[(3-nitrophenyl)methylideneamino]urea Structure

1,3-bis[(3-nitr...

Potassium carbonate Structure

Potassium carbonate

Benzaldehyde Structure

~90%

Carbonic dihydrazide,2,2'-bis(phenylmethylene)- Structure

Carbonic dihydr...

Benzenesulfonic acid,4-methyl-, 2-(phenylmethylene)hydrazide Structure

Benzenesulfonic...

Potassium carbonate Structure

Potassium carbonate

~92%

Carbonic dihydrazide,2,2'-bis(phenylmethylene)- Structure

Carbonic dihydr...

1-(diethoxyphosphoryl)-2-(phenylmethylidene)hydrazine Structure

1-(diethoxyphos...

Potassium carbonate Structure

Potassium carbonate

~78%

Carbonic dihydrazide,2,2'-bis(phenylmethylene)- Structure

Carbonic dihydr...

Benzaldehyde Structure

~%

Carbonic dihydrazide,2,2'-bis(phenylmethylene)- Structure

Carbonic dihydr...