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

" Tert-Amino effect" in heterocyclic synthesis. Formation of N heterocycles by ring-closure reactions of substituted 2-vinyl-N, N-dialkylanilines

W Verboom, DN Reinhoudt, R Visser…

Index: Verboom, Willem; Reinhoudt, David N.; Visser, Richard; Harkema, Sybolt Journal of Organic Chemistry, 1984 , vol. 49, # 2 p. 269 - 276

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Citation Number: 95

Abstract

5b, c and the (4-morpholiny1) benzeneacetonitrile 7c do not react. The (1-piperidiny1) benzeneacetonitrile 7b yields in refluxing toluene in the presence of zinc chloride the pyrido [l, 2-a] indole 14b and, by HCN elimination, pyrido [l, 2-a] indole 15b. Under these ...

2-Bromoaniline Structure

~%

dimethyl 2-(2-morpholin-4-ylphenyl)but-2-enedioate Structure

dimethyl 2-(2-m...

N-(2-Bromophenyl)morpholine Structure

N-(2-Bromopheny...

Dimethyl but-2-ynedioate Structure

Dimethyl but-2-...

~%

dimethyl 2-(2-morpholin-4-ylphenyl)but-2-enedioate Structure

dimethyl 2-(2-m...

2-Bromoaniline Structure

~%

dimethyl 2-(2-pyrrolidin-1-ylphenyl)but-2-enedioate Structure

dimethyl 2-(2-p...

1-(2-Bromophenyl)pyrrolidine Structure

1-(2-Bromopheny...

Dimethyl but-2-ynedioate Structure

Dimethyl but-2-...

~%

dimethyl 2-(2-pyrrolidin-1-ylphenyl)but-2-enedioate Structure

dimethyl 2-(2-p...

2-(1-Pyrrolidinyl)benzaldehyde Structure

2-(1-Pyrrolidin...

~%

ethyl 3-(2-pyrrolidin-1-ylphenyl)prop-2-enoate Structure

ethyl 3-(2-pyrr...

2-(1-Pyrrolidinyl)benzaldehyde Structure

2-(1-Pyrrolidin...

Dimethyl malonate Structure

Dimethyl malonate

~76%

dimethyl 2-[(2-pyrrolidin-1-ylphenyl)methylidene]propanedioate Structure

dimethyl 2-[(2-...

2-(1-Pyrrolidinyl)benzaldehyde Structure

2-(1-Pyrrolidin...

Malononitrile Structure

~88%

2-[(2-pyrrolidin-1-ylphenyl)methylidene]propanedinitrile Structure

2-[(2-pyrrolidi...

1,4-Dibromobutane Structure

1,4-Dibromobutane

2-Bromoaniline Structure

~87%

1-(2-Bromophenyl)pyrrolidine Structure

1-(2-Bromopheny...

2-(Piperidin-1-yl)benzaldehyde Structure

2-(Piperidin-1-...

Malononitrile Structure

~91%

2-[(2-piperidin-1-ylphenyl)methylidene]propanedinitrile Structure

2-[(2-piperidin...

Bis(2-bromoethyl) ether Structure

Bis(2-bromoethy...

2-Bromoaniline Structure

~51%

N-(2-Bromophenyl)morpholine Structure

N-(2-Bromopheny...

2-Morpholinobenzaldehyde Structure

2-Morpholinoben...

Malononitrile Structure

~90%

2-[(2-morpholin-4-ylphenyl)methylidene]propanedinitrile Structure

2-[(2-morpholin...

cis-2,3,9,9a-Tetrahydro-9-(phenylmethyl)-1H-pyrrolo(1,2-a)indole-9-carbonitrile Structure

cis-2,3,9,9a-Te...

~62%

4-benzyl-2,3-dihydro-1H-pyrrolo[1,2-a]indole Structure

4-benzyl-2,3-di...

α-(Phenylmethylene)-2-(1-piperidinyl)-benzeneacetonitrile Structure

α-(Phenylmethyl...

~26%

10-benzyl-6,7,8,9-tetrahydropyrido[1,2-a]indole Structure

10-benzyl-6,7,8...

6,7,8,9,9a,10-Hexahydro-10-(phenylmethyl)pyrido(1,2-a)indole-10-carbonitrile Structure

6,7,8,9,9a,10-H...

1,5-Dibromopentane Structure

1,5-Dibromopentane

~%

10-benzyl-6,7,8,9-tetrahydropyrido[1,2-a]indole Structure

10-benzyl-6,7,8...

N/A Structure

~%

10-benzyl-6,7,8,9-tetrahydropyrido[1,2-a]indole Structure

10-benzyl-6,7,8...

1,5-Dibromopentane Structure

1,5-Dibromopentane

~%

dimethyl 2-(2-piperidin-1-ylphenyl)but-2-enedioate Structure

dimethyl 2-(2-p...

2-Bromoaniline Structure

~%

dimethyl 2-(2-piperidin-1-ylphenyl)but-2-enedioate Structure

dimethyl 2-(2-p...

4-(2-Bromophenyl)piperidine Structure

4-(2-Bromopheny...

Dimethyl but-2-ynedioate Structure

Dimethyl but-2-...

~%

dimethyl 2-(2-piperidin-1-ylphenyl)but-2-enedioate Structure

dimethyl 2-(2-p...