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

Tetrahedron

Carbon transfer reactions of Δ 2-oxazolinium and thiazolinium cations

H Singh, R Sarin

Index: Singh, Harjit; Sarin, Rakesh Tetrahedron, 1986 , vol. 42, # 5 p. 1449 - 1460

Full Text: HTML

Citation Number: 10

Abstract

Δ2-Oxazolinium and thiazolinium cations with or without an appendage at any of the heteroatoms transfer their C (2) units at the carboxylic acid oxidation level to binucleophiles and provide the corresponding heterocycles, thus mimicking carbon transfer reactions exhibited by THF models, N-methyl N'-tosyl/acetyl imidazolinium cations. However, these azolinium cations react with phen ethyl amine and tryptamine to furnish their N-acyl ...

2,3-DIMETHYLTHIAZOLINIUM IODIDE Structure

2,3-DIMETHYLTHI...

~50%

N-(2-Mercaptoethyl)-N-methylacetamide Structure

N-(2-Mercaptoet...

4,4-Dimethyl-2-phenyl-2-oxazoline Structure

4,4-Dimethyl-2-...

~%

4,4-dimethyl-2-phenyl-5H-1,3-oxazole,hydrochloride Structure

4,4-dimethyl-2-...

2-phenyl-4,5-dihydro-1,3-thiazole Structure

2-phenyl-4,5-di...

~%

4,4-dimethyl-2-phenyl-5H-1,3-oxazole,hydrochloride Structure

4,4-dimethyl-2-...

3-methyl-2-phenyl-4,5-dihydro-1,3-thiazol-3-ium,iodide Structure

3-methyl-2-phen...

~%

4,4-dimethyl-2-phenyl-5H-1,3-oxazole,hydrochloride Structure

4,4-dimethyl-2-...

N/A Structure

~%

4,4-dimethyl-2-phenyl-5H-1,3-oxazole,hydrochloride Structure

4,4-dimethyl-2-...

Thiobenzamide Structure

~%

4,4-dimethyl-2-phenyl-5H-1,3-oxazole,hydrochloride Structure

4,4-dimethyl-2-...

2-phenyl-4,5-dihydro-1,3-thiazole Structure

2-phenyl-4,5-di...

~%

2-phenyl-1,4,5,6-tetrahydropyrimidine Structure

2-phenyl-1,4,5,...

N/A Structure

~%

2-phenyl-1,4,5,6-tetrahydropyrimidine Structure

2-phenyl-1,4,5,...

Thiobenzamide Structure

~%

2-phenyl-1,4,5,6-tetrahydropyrimidine Structure

2-phenyl-1,4,5,...

4,4-Dimethyl-2-phenyl-2-oxazoline Structure

4,4-Dimethyl-2-...

~%

2-phenyl-1,4,5,6-tetrahydropyrimidine Structure

2-phenyl-1,4,5,...

3-methyl-2-phenyl-4,5-dihydro-1,3-thiazol-3-ium,iodide Structure

3-methyl-2-phen...

~%

2-phenyl-1,4,5,6-tetrahydropyrimidine Structure

2-phenyl-1,4,5,...

2-phenyl-4,5-dihydro-1,3-thiazole Structure

2-phenyl-4,5-di...

methyl iodide Structure

~60%

3-methyl-2-phenyl-4,5-dihydro-1,3-thiazol-3-ium,iodide Structure

3-methyl-2-phen...

N/A Structure

~%

3-methyl-2-phenyl-4,5-dihydro-1,3-thiazol-3-ium,iodide Structure

3-methyl-2-phen...

Thiobenzamide Structure

~%

3-methyl-2-phenyl-4,5-dihydro-1,3-thiazol-3-ium,iodide Structure

3-methyl-2-phen...

Oxazole, 4,5-dihydro-4,4-dimethyl-, hydrochloride (1:1) Structure

Oxazole, 4,5-di...

o-Phenylenediamine Structure

o-Phenylenediamine

~82%

Benzimidazole Structure

N/A Structure

aminophenol Structure

~10%

2-Phenylbenzoxazole Structure

2-Phenylbenzoxazole

2,3-DIMETHYLTHIAZOLINIUM IODIDE Structure

2,3-DIMETHYLTHI...

2-Phenylethanamine Structure

2-Phenylethanamine

~18%

N-(2-Phenylethyl)acetamide Structure

N-(2-Phenylethy...

2,3,4,4-tetramethyl-2-oxazolinium iodide Structure

2,3,4,4-tetrame...

2-Phenylethanamine Structure

2-Phenylethanamine

~17%

N-(2-Phenylethyl)acetamide Structure

N-(2-Phenylethy...

Oxazole, 4,5-dihydro-4,4-dimethyl-, hydrochloride (1:1) Structure

Oxazole, 4,5-di...

aminophenol Structure

~56%

Formamide,N-(2-hydroxyphenyl)- Structure

Formamide,N-(2-...

tryptamine Structure

2,3-DIMETHYLTHIAZOLINIUM IODIDE Structure

2,3-DIMETHYLTHI...

~20%

N-Acetyltryptamine Structure

N-Acetyltryptamine

tryptamine Structure

2,3,4,4-tetramethyl-2-oxazolinium iodide Structure

2,3,4,4-tetrame...

~20%

N-Acetyltryptamine Structure

N-Acetyltryptamine

4,4-Dimethyl-2-phenyl-2-oxazoline Structure

4,4-Dimethyl-2-...

~%

2-phenyl-4,5-dihydro-1,3-thiazole Structure

2-phenyl-4,5-di...

3-methyl-2-phenyl-4,5-dihydro-1,3-thiazol-3-ium,iodide Structure

3-methyl-2-phen...

~%

2-phenyl-4,5-dihydro-1,3-thiazole Structure

2-phenyl-4,5-di...

1,2-Dibromoethane Structure

1,2-Dibromoethane

Thiobenzamide Structure

~65%

2-phenyl-4,5-dihydro-1,3-thiazole Structure

2-phenyl-4,5-di...

2-Fenil-5-idrossi-1,3,4-triazolo [Italian] Structure

2-Fenil-5-idros...

~70%

5-phenyl-4h-1,2,4-triazole-3-thiol Structure

5-phenyl-4h-1,2...

N/A Structure

o-Phenylenediamine Structure

o-Phenylenediamine

~61%

2-Phenyl-1H-benzo[d]imidazole Structure

2-Phenyl-1H-ben...