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

Hindered ureas as masked isocyanates: Facile carbamoylation of nucleophiles under neutral conditions

…, GC Lloyd??Jones, KI Booker??Milburn

Index: Hutchby, Marc; Houlden, Chris E.; Gair Ford; Tyler, Simon N. G.; Gagne, Michel R.; Lloyd-Jones, Guy C.; Booker-Milburn, Kevin I. Angewandte Chemie - International Edition, 2009 , vol. 48, # 46 p. 8721 - 8724

Full Text: HTML

Citation Number: 44

Abstract

Ureas are normally rather inert towards alcohols, amines, and thiols: they require high temperatures, acidic or basic conditions, or metal catalysis, to undergo nucleophilic substitution reactions.[1] Whilst this feature makes them robust protecting groups for aromatic and aliphatic amines, it somewhat limits their subsequent utility. Herein we demonstrate that, in stark contrast to this general behavior, hindered trisubstituted ureas ...

Methanol Structure

3-tert-butyl-1,1-diisopropylurea Structure

3-tert-butyl-1,...

~0%

methyl N-tert-butylcarbamate Structure

methyl N-tert-b...

Diisopropylamine Structure

Diisopropylamine

1-tert-butyl-1-ethyl-3-phenylurea Structure

1-tert-butyl-1-...

Benzyl alcohol Structure

~96%

Carbamic acid,N-phenyl-,phenylmethyl ester Structure

Carbamic acid,N...

methyl 2-(3,3-diisopropylureido)benzoate Structure

methyl 2-(3,3-d...

~89%

Anthranilic acid Structure

Anthranilic acid

Methanol Structure

1-tert-butyl-1-methyl-3-phenylurea Structure

1-tert-butyl-1-...

~0%

n-methyl-tert-butylamine Structure

n-methyl-tert-b...

Carbamic acid,N-phenyl-,methyl ester Structure

Carbamic acid,N...

Methanol Structure

1-Propanol Structure

Ethanol Structure

1-tert-butyl-1-ethyl-3-phenylurea Structure

1-tert-butyl-1-...

~21%

Detail

Methanol Structure

1-Propanol Structure

Ethanol Structure

Phenylisocyanate Structure

Phenylisocyanate

~22%

Detail

Methanol Structure

N/A Structure

~%

methyl (4-nitrophenyl)carbamate Structure

methyl (4-nitro...

Diisopropylamine Structure

Diisopropylamine

Methanol Structure

1-tert-butyl-1-isopropyl-3-phenylurea Structure

1-tert-butyl-1-...

~96%

N-tert-Butylisopropylamine Structure

N-tert-Butyliso...

Carbamic acid,N-phenyl-,methyl ester Structure

Carbamic acid,N...

Methanol Structure

1-tert-butyl-3-phenyl-1-propylurea Structure

1-tert-butyl-3-...

~10%

2-methyl-N-propylpropan-2-amine Structure

2-methyl-N-prop...

Carbamic acid,N-phenyl-,methyl ester Structure

Carbamic acid,N...

Methanol Structure

1-tert-butyl-1-methyl-3-phenylurea Structure

1-tert-butyl-1-...

~99%

n-methyl-tert-butylamine Structure

n-methyl-tert-b...

Carbamic acid,N-phenyl-,methyl ester Structure

Carbamic acid,N...

Methanol Structure

1-Propanol Structure

Ethanol Structure

1-tert-butyl-1-ethyl-3-phenylurea Structure

1-tert-butyl-1-...

~45%

Detail

Methanol Structure

1-Propanol Structure

Ethanol Structure

Phenylisocyanate Structure

Phenylisocyanate

~46%

Detail

Methanol Structure

1-tert-butyl-1-ethyl-3-phenylurea Structure

1-tert-butyl-1-...

~%

n-tert-butylethylamine Structure

n-tert-butyleth...

Carbamic acid,N-phenyl-,methyl ester Structure

Carbamic acid,N...

Methanol Structure

1-tert-butyl-1-isopropyl-3-phenylurea Structure

1-tert-butyl-1-...

~0%

N-tert-Butylisopropylamine Structure

N-tert-Butyliso...

Carbamic acid,N-phenyl-,methyl ester Structure

Carbamic acid,N...

Methanol Structure

1,3-di-tert-butyl-1-isopropylurea Structure

1,3-di-tert-but...

~0%

methyl N-tert-butylcarbamate Structure

methyl N-tert-b...

N-tert-Butylisopropylamine Structure

N-tert-Butyliso...

1-tert-butyl-1-ethyl-3-phenylurea Structure

1-tert-butyl-1-...

tert-Butanol Structure

~68%

N-BOC-aniline Structure

Methanol Structure

1-tert-butyl-1-ethyl-3-phenylurea Structure

1-tert-butyl-1-...

~98%

Carbamic acid,N-phenyl-,methyl ester Structure

Carbamic acid,N...

Methanol Structure

N/A Structure

~%

Carbamic acid,N-phenyl-,methyl ester Structure

Carbamic acid,N...

Diisopropylamine Structure

Diisopropylamine

Methanol Structure

1-tert-butyl-3-phenyl-1-propylurea Structure

1-tert-butyl-3-...

~0%

2-methyl-N-propylpropan-2-amine Structure

2-methyl-N-prop...

Carbamic acid,N-phenyl-,methyl ester Structure

Carbamic acid,N...

1-tert-butyl-1-ethyl-3-phenylurea Structure

1-tert-butyl-1-...

~96%

1,3-Diphenylurea Structure

1,3-Diphenylurea

Methanol Structure

1-tert-butyl-1-ethyl-3-phenylurea Structure

1-tert-butyl-1-...

~%

n-tert-butylethylamine Structure

n-tert-butyleth...

Carbamic acid,N-phenyl-,methyl ester Structure

Carbamic acid,N...

1-tert-butyl-1-ethyl-3-phenylurea Structure

1-tert-butyl-1-...

Thiophenol Structure

~62%

N-phenyl-1-phenylsulfanyl-formamide Structure

N-phenyl-1-phen...

Methanol Structure

1,1-diisopropyl-3-(3-nitrophenyl)urea Structure

1,1-diisopropyl...

~%

methyl N-(3-nitrophenyl)carbamate Structure

methyl N-(3-nit...

Diisopropylamine Structure

Diisopropylamine

Methanol Structure

1,1-diisopropyl-3-(3-methoxyphenyl)urea Structure

1,1-diisopropyl...

~%

(3-Methoxyphenyl)carbamic acid methyl ester Structure

(3-Methoxypheny...

Diisopropylamine Structure

Diisopropylamine

1-tert-butyl-1-ethyl-3-phenylurea Structure

1-tert-butyl-1-...

Phenol Structure

~72%

Phenyl phenylcarbamate Structure

Phenyl phenylca...

A facile synthesis of symmetrical secondary amines from prim...

[Bui-The-Khai; Concilio, Carlo; Porzi, Gianni Journal of Organometallic Chemistry, 1981 , vol. 208, # 2 p. 249 - 251]

Palladium-catalyzed reaction of allyl carbamates; allylation...

[Minami, Ichiro; Ohashi, Yukihiro; Shimizu, Isao; Tsuji, Jiro Tetrahedron Letters, 1985 , vol. 26, # 20 p. 2449 - 2452]

New synthetic route to unsymmetrically substituted pentacoor...

[Journal of the American Chemical Society, , vol. 112, # 23 p. 8575 - 8577]

New synthetic route to unsymmetrically substituted pentacoor...

[Journal of the American Chemical Society, , vol. 112, # 23 p. 8575 - 8577]

New synthetic route to unsymmetrically substituted pentacoor...

[Journal of the American Chemical Society, , vol. 112, # 23 p. 8575 - 8577]