Online citations, reference lists, and bibliographies.
← Back to Search

Effective Approach To Ureas Through Organocatalyzed One-pot Process

M. Wang, Jilai Han, Xiaojia Si, Y. Hu, Jidong Zhu, Xun Sun
Published 2017 · Chemistry

Cite This
Download PDF
Analyze on Scholarcy
Share
Abstract An efficient approach to N, N′-unsymmetrically substituted ureas 9 has been developed through the ammonolysis process of N-Boc protected anilines 7 with amines prompted by 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). Moreover, a convenient protocol for the synthesis of the symmetric N, N'-substituted ureas 12 by one-pot diammonolysis process of Boc2O with amines catalyzed by DABCO has also been achieved. With broad substrate scope and mild conditions, these two methods demonstrate practical preparation of both unsymmetrical and symmetrical ureas.
This paper references
10.1021/cr4005605
Application of the intermediate derivatization approach in agrochemical discovery.
A. Guan (2014)
10.1021/jo500492x
One-pot synthesis of ureas from Boc-protected amines.
C. Spyropoulos (2014)
10.1002/EJOC.200700148
Transition metal-catalyzed oxidative carbonylation of amines to ureas
Delmy J. Diaz (2007)
10.1039/B002127J
Selected syntheses of ureas through phosgenesubstitutes
F. Bigi (2000)
10.1016/J.BMCL.2006.03.030
Discovery of SB-705498: a potent, selective and orally bioavailable TRPV1 antagonist suitable for clinical development.
H. K. Rami (2006)
10.1021/JO962245T
A General Synthesis of Unsymmetrical Tetrasubstituted Ureas
A. R. Katritzky (1997)
10.1002/EJOC.201100657
Catalytic Oxidative Carbonylation of Arylamines to Ureas with W(CO)6/I2 as Catalyst
L. Zhang (2011)
10.1002/APP.34135
Synthesis and properties of polyurethane-urea-based liquid bandage materials
Soojeong Choi (2011)
10.1039/B612403H
Synthesis of symmetrical or asymmetrical urea compounds from CO2via base catalysis
A. Ion (2007)
10.1021/ol101474f
Acetoacetanilides as masked isocyanates: facile and efficient synthesis of unsymmetrically substituted ureas.
Y. Wei (2010)
10.1016/j.ejmech.2016.02.021
Discovery of novel sesquistilbene indanone analogues as potent anti-inflammatory agents.
M. Tang (2016)
10.1002/ANIE.199524971
A Novel Method for the Synthesis of Isocyanates Under Mild Conditions
H. Knölker (1995)
10.1039/c3cc42381f
Copper catalyzed oxidative coupling of amines with formamides: a new approach for the synthesis of unsymmetrical urea derivatives.
G. Kumar (2013)
10.1021/jf3001229
Urea-montmorillonite-extruded nanocomposites: a novel slow-release material.
E. Pereira (2012)
10.1021/JM0306226
Synthesis of urea-based inhibitors as active site probes of glutamate carboxypeptidase II: efficacy as analgesic agents.
A. Kozikowski (2004)
10.1021/jm301085w
Vascular endothelial growth factor (VEGF) receptors: drugs and new inhibitors.
F. Musumeci (2012)
10.1021/JM020057R
Pyrazole urea-based inhibitors of p38 MAP kinase: from lead compound to clinical candidate.
J. Regan (2002)
10.1002/ANIE.200701489
DABCO and DMAP--why are they different in organocatalysis?
M. Baidya (2007)
10.1021/JO00086A061
A safe and efficient method for preparation of N,N'-unsymmetrically disubstituted ureas utilizing triphosgene
P. Majer (1994)
10.1021/ACS.OPRD.7B00019
Synthesis of Urea Derivatives in Two Sequential Continuous-Flow Reactors
P. Bana (2017)
10.1016/J.TETLET.2016.09.038
One-pot synthesis of carbamates and thiocarbamates from Boc-protected amines
H. Kim (2016)
10.1021/JO0494634
Efficient synthesis of ureas by direct palladium-catalyzed oxidative carbonylation of amines.
B. Gabriele (2004)
10.1021/jo302084a
Synthesis and reactivity of N-alkyl carbamoylimidazoles: development of N-methyl carbamoylimidazole as a methyl isocyanate equivalent.
Petar A. Duspara (2012)
10.1126/science.1182826
Asymmetric Cooperative Catalysis of Strong Brønsted Acid–Promoted Reactions Using Chiral Ureas
H. Xu (2010)
10.1021/jm401780b
Design, synthesis, and biological evaluation of deuterated C-aryl glycoside as a potent and long-acting renal sodium-dependent glucose cotransporter 2 inhibitor for the treatment of type 2 diabetes.
Ge Xu (2014)
10.1021/acs.orglett.6b00381
Pd/C Catalyzed Carbonylation of Azides in the Presence of Amines.
J. Zhao (2016)
10.1021/CR068373R
Small-molecule H-bond donors in asymmetric catalysis.
A. G. Doyle (2007)
10.1039/C2MD20044A
Small molecules targeting phosphoinositide 3-kinases
P. Wu (2012)
10.1016/J.BMCL.2005.03.049
Benzimidazolones and indoles as non-thiol farnesyltransferase inhibitors based on tipifarnib scaffold: synthesis and activity.
Q. Li (2005)
10.1039/c3ob41517a
Urea-catalyzed construction of oxazinanes.
Andrea M. Hardman (2013)
10.1039/B211740A
A novel and efficient method for the Pd-catalysed oxidative carbonylation of amines to symmetrically and unsymmetrically substituted ureas.
B. Gabriele (2003)
10.1021/JA075653V
Enantioselective aza-Henry reaction with an N-sulfinyl urea organocatalyst.
MaryAnn T. Robak (2007)
10.1021/ja8063292
Catalytic enantioselective additions of indoles to nitroalkenes.
Madhu Ganesh (2008)
10.1021/acs.joc.6b02521
Scalable, One-Pot, Microwave-Accelerated Tandem Synthesis of Unsymmetrical Urea Derivatives.
A. Kulkarni (2017)
10.1016/j.bmcl.2013.05.058
Inhibitory effect of resveratrol dimerized derivatives on nitric oxide production in lipopolysaccharide-induced RAW 264.7 cells.
C. Zhong (2013)
10.1021/ol202873d
Boronate urea activation of nitrocyclopropane carboxylates.
Sonia S. So (2012)
10.1002/chem.201603664
Sulfoxide-Based Enantioselective Nazarov Cyclization: Divergent Syntheses of (+)-Isopaucifloral F, (+)-Quadrangularin A, and (+)-Pallidol.
M. Tang (2016)
10.1080/00304940709458592
UNSYMMETRICAL UREAS. SYNTHETIC METHODOLOGIES AND APPLICATION IN DRUG DESIGN
I. Gallou (2007)
10.1016/J.BMCL.2005.05.082
SAR studies of 6-aryl-1,3-dihydrobenzimidazol-2-ones as progesterone receptor antagonists.
E. Terefenko (2005)
10.1039/c3cc47590e
A copper-mediated tandem reaction through isocyanide insertion into N-H bonds: efficient access to unsymmetrical tetrasubstituted ureas.
X. Huang (2014)
10.1039/B717868A
Solvent-free synthesis of substituted ureas from CO2 and amines with a functional ionic liquid as the catalyst
T. Jiang (2008)
10.1021/acs.orglett.5b03328
Ruthenium-Catalyzed Urea Synthesis Using Methanol as the C1 Source.
S. H. Kim (2016)



This paper is referenced by
Semantic Scholar Logo Some data provided by SemanticScholar