2-Phenyl-tetrahydropyrimidine-4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids

2-Phenyl-tetrahydropyrimidine-4(1H)-ones – cyclic benzaldehyde aminals as precursors for functionalised β2-amino acids

Novel procedures have been developed to condense benzaldehyde effectively with β-amino acid amides to cyclic benzyl aminals. Double carbamate protection of the heterocycle resulted in fully protected chiral β-alanine derivatives. These serve as universal precursors for the asymmetric synthesis of fu...

Full description

Bibliographic Details
Main Authors:	Markus Nahrwold, Arvydas Stončius, Anna Penner, Beate Neumann, Hans-Georg Stammler, Norbert Sewald
Format:	Article
Language:	English
Published:	Beilstein-Institut 2009-09-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	β2-amino acids cyclocondensation diastereoselective alkylation N,N-acetals peptidomimetics ring opening self-regeneration of stereocentres (SRS)
Online Access:	https://doi.org/10.3762/bjoc.5.43

Similar Items

Microwave assisted synthesis of some novel acetazolamide cyclocondensed 1,2,3,4-tetrahydropyrimidines as a potent antimicrobial and cytotoxic agents
by: Karthikeyan Elumalai, et al.
Published: (2014-03-01)

Novel isoniazid cyclocondensed 1,2,3,4-tetrahydropyrimidine derivatives for treating infectious disease: a synthesis and in vitro biological evaluation
by: Karthikeyan Elumalai, et al.
Published: (2013-01-01)

TDAE Strategy for the Synthesis of 2,3-Diaryl N-Tosylaziridines
by: Thierry Terme, et al.
Published: (2013-06-01)

An efficient synthesis of novel 3’-substituted 2-aryl-5-methyl-5'thioxo-[4,4'-bi-4H-1,2,4-triazol]-3(1'H, 2H)-ones
by: Kamble Ravindra R., et al.
Published: (2006-01-01)

An efficient synthesis of novel 3’-substituted 2-aryl-5-methyl-5'thioxo-[4,4'-bi-4H-1,2,4-triazol]-3(1'H, 2H)-ones
by: RAVINDRA R. KAMBLE, et al.
Published: (2006-04-01)

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues
by: Charlotte Collet, et al.
Published: (2016-02-01)

Enantioselective synthesis of b-Amino acids. 12. experimental and theoretical study of the diastereoselectivity of alkylation of the dianion of N',N'-Bis(a-phenylethyl)-N -carbobenzyloxypropionamide
by: Gutiérrez-García Víctor Manuel, et al.
Published: (2001-01-01)

Bis-(1-phenyl-5-nitro-6-methylthio-1,2,3,4-tetrahydropyrimidinyl)benzene and Bis-(1-phenyl-5-nitro-6-methylthio-1,2,3,4-tetrahydropyrimidinyl)diphenyl
by: J.N. Vishwakarma, et al.
Published: (2005-08-01)

An Efficient Synthetic Approach Towards Benzo[<i>b</i>]pyrano[2,3-<i>e</i>][1,4]diazepines, and Their Cytotoxic Activity
by: Islam H. El Azab, et al.
Published: (2020-04-01)

Hybrid Molecules Containing a 7-Chloro-4-aminoquinoline Nucleus and a Substituted 2-Pyrazoline with Antiproliferative and Antifungal Activity
by: Alba Montoya, et al.
Published: (2016-07-01)

Chimie des acrylamides chiraux : nouvelles méthodologies et application à la synthèse de nouvelles architectures moléculaires
by: Gratais, Alexandre
Published: (2014)

Asymmetric Hydrogenations of Chiral Acyclic Alkenes for Important Chiron Syntheses
by: Zhu, Ye
Published: (2012)

1-[3-(2-Methyl-4-phenylquinolin-3-yl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-propane-1-one
by: Allaoua Kedjadja, et al.
Published: (2015-06-01)

Synthesis and DFT Calculations of Novel Vanillin-Chalcones and Their 3-Aryl-5-(4-(2-(dimethylamino)-ethoxy)-3-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbaldehyde Derivatives as Antifungal Agents
by: Luis Alberto Illicachi, et al.
Published: (2017-09-01)

Hybrid hetarylhydrazones and enamines of Furan-2(3H)-ones as a framework for the synthesis of poly-N-heterocycles
by: Oksana A. Mayorova, et al.
Published: (2021-02-01)

Syntheses of 3,4- and 1,4-dihydroquinazolines from 2-aminobenzylamine
by: Jimena E. Díaz, et al.
Published: (2017-07-01)

5-(4-Bromophenyl)-7-(2,4-dimethoxyphenyl)-4,7-dihydrotetrazolo[1,5-<em>a</em>]pyrimidine
by: Kautsar Ul Haq, et al.
Published: (2018-12-01)

Similarity analysis, synthesis, and bioassay of antibacterial cyclic peptidomimetics
by: Workalemahu M. Berhanu, et al.
Published: (2012-07-01)

N-alkylation of amines via dehydrogenative coupling with alcohol catalyzed by the well-defined PN3 rhenium pincer complex
by: Alobaid, Nasser A.
Published: (2020)

1,1′-{1,4-Phenylene bis[3-(6-chloro-2-methyl-4-phenylquinolin-3-yl)-4,5-dihydro-1H-pyrazole-5,1-diyl]}dibutan-1-one
by: Allaoua Kedjadja, et al.
Published: (2015-10-01)

Synthesis of Novel Fused Heterocycles Based on Pyrano[2,3-c]pyrazole
by: M. E. A. Zaki
Published: (1998-02-01)

Diastereoselective functionalisation of benzo-annulated bicyclic sultams: Application for the synthesis of cis-2,4-diarylpyrrolidines
by: Susan Kelleher, et al.
Published: (2009-11-01)

4’-(N-(propan-1,2-dienyl)pyrrol-2-yl)-2,2’:6’,2’’-terpyridine
by: Jérôme Husson, et al.
Published: (2020-06-01)

2-Hydroxy-3-(4-oxy(2,2,6,6-tetramethylpiperidin-1-oxyl)butoxy)benzaldehyde
by: Anatoliy A. Vereshchagin, et al.
Published: (2021-07-01)

Recent Advances in the Synthesis of Spiroheterocycles via N-Heterocyclic Carbene Organocatalysis
by: Yue Liu, et al.
Published: (2017-11-01)

Synthesis of N-and N,N-dialkyl-S-alkylthiolcarbamates by the rearrangement of N-and N,N-dialkyl-O-thioncarbamates
by: Milosavljević Milutin M., et al.
Published: (2006-01-01)

Methyl N-[1-(Benzoylamino)-2-methoxy-2-oxoethyl]-tryptophanate
by: Oumaima Karai, et al.
Published: (2017-09-01)

Synthesis of 5-(substituted phenylazo)-6-hydroxy-4-methyl-3-cyano-2-pyridones from ethyl 3-oxo-2-(substituted phenylazo)butanoates, Short communication
by: GORDANA UŠĆUMLIĆ, et al.
Published: (2011-04-01)

Efficient Microwave-Assisted Synthesis of 5-Deazaflavine Derivatives
by: Justo Cobo, et al.
Published: (2010-10-01)

Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles
by: Olga V. Petrova, et al.
Published: (2021-03-01)

A microwave approach to the synthesis of certain 4-substituted phenyl-6-phenyl-3-cyano-2-pyridones
by: Marinković Aleksandar, et al.
Published: (2014-01-01)

Diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative
by: Tomoko Yajima, et al.
Published: (2013-07-01)

Diastereoselective α-Alkylation of Chiral β-Borylated Esters
by: Perfetti, Michael Thomas
Published: (2014)

Synthetic route towards potential bivalent ligands possessing opioid and D2/D3 pharmacophores
by: Jevtić Ivana I., et al.
Published: (2019-01-01)

(<em>R</em>,<em>S</em>)-5-(4-Chlorophenyl)-3-{(<em>E</em>)-2-[(<em>R</em>,<em>S</em>)-2,6,6-trimethylcyclohex-2-en-1-yl]vinyl}-4,5-dihydro-1<em>H</em>-pyrazole-1-carboximidamide Hydrochloride
by: Michele Cristina Carvalho, et al.
Published: (2019-02-01)

Crystal structure of 2-(2,6-diisopropylphenyl)-N,N-diethyl-3,3-dimethyl-2-azaspiro[4.5]decan-1-amine: a diethylamine adduct of a cyclic(alkyl)(amino)carbene (CAAC)
by: Roxanne A. Naumann, et al.
Published: (2021-09-01)

N-Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity
by: Agata Walczewska, et al.
Published: (2015-05-01)

An improved synthesis of adefovir and related analogues
by: David J. Jones, et al.
Published: (2019-03-01)

Synthesis and Characterization of 1-(1-chlorocyclopropyl)-2-(1,2,4-triazol-1-yl)ethan-1-one
by: Ji Haifeng, et al.
Published: (2017-03-01)

Pd@[nBu4][Br] as a Simple Catalytic System for N-Alkylation Reactions with Alcohols
by: Bastien Cacciuttolo, et al.
Published: (2016-08-01)

Cannot write session to /tmp/vufind_sessions/sess_6ojv7fpbbsm969q3qmprvn258i