Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic.

ABSTRACT: A substituted hydropyrazino[1,2-a]pyrimidin-6-one derivative was synthesized stereoselectively via the intramolecular N-acyliminium ion cyclization between an amide nitrogen and an N(?)-acetal derived from Cbz-protected aminopropyl-phenylalaninamide in very good yields. The formation of a single diastereomer is due to the low energy chairlike conformation of its bicyclic structure. This methodology provides a convenient tool to build internal bicyclic peptidomimetics.

SUBMITTER: Min BJ

PROVIDER: S-EPMC2390882 | biostudies-literature | 2008 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Synthesis of a novel benzyl-octahydropyrazino[1,2-a]pyrimidin-6-one derivative as a convenient internal bicyclic peptidomimetic.

Min Byoung J BJ Gu Xuyuan X Yamamoto Takashi T Petrov Ravil R RR Qu Hongchang H Lee Yeon Sun YS Hruby Victor J VJ

Tetrahedron letters 20080301 14

A substituted hydropyrazino[1,2-a]pyrimidin-6-one derivative was synthesized stereoselectively via the intramolecular N-acyliminium ion cyclization between an amide nitrogen and an N(α)-acetal derived from Cbz-protected aminopropyl-phenylalaninamide in very good yields. The formation of a single diastereomer is due to the low energy chairlike conformation of its bicyclic structure. This methodology provides a convenient tool to build internal bicyclic peptidomimetics. ...[more]

PMID: 19340283

Similar Datasets

Crystal structure of (E)-9-(4-nitro-benzyl-idene)-8,9-di-hydro-pyrido[2,3-d]pyrrolo-[1,2-a]pyrimidin-5(7H)-one.

Project description:The title compound, C17H12N4O3, a pyrido-pyrrolo-pyrimidine derivative, is almost planar. The nitro-benzene ring is inclined to the mean plane of the 8,9-di-hydro-pyrido[2,3-d]pyrrolo-[1,2-a]pyrimidin-5(7H)-one moiety (r.m.s. deviation = 0.023 Å) by 6.8 (1)°. In the crystal, mol-ecules are linked via C-H⋯O and C-H⋯N hydrogen bonds, forming layers parallel to (101).

| S-EPMC4910333 | biostudies-literature

Convenient access to bicyclic and tricyclic diazenes.

Project description:Heating the tosylhydrazone of an omega-alkenyl ketone or aldehyde to reflux in toluene in the presence of K(2)CO(3) delivered the bicyclic diazene. Irradiation of the diazene converted it to the cyclopropane. This appears to be a generally useful method for the construction of substituted cyclopentanes and cyclohexanes.

| S-EPMC2765546 | biostudies-literature

2-Tri-fluoro-methyl-10H-benzo[4,5]imidazo[1,2-a]pyrimidin-4-one.

Project description:In the mol-ecule of the title compound, C11H6F3N3O, the three fused rings of the benzo[4,5]imidazo[1,2-a]pyrimidine unit are essentially coplanar, the maximum deviation from the mean plane being 0.096?(2)?Å. In the crystal, N-H?O hydrogen bonds link the mol-ecules into chains running along the b-axis direction.

| S-EPMC3790404 | biostudies-literature

3-(2-Chloro-ethyl)-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one.

Project description:In the title mol-ecule, C(11)H(11)ClN(2)O, the pyrido[1,2-a]pyrimidine ring system is planar (maximum deviation = 0.0148?Å) and the methyl C and carbonyl O atoms are nearly coplanar to it. The chloro-ethyl side chain is in a synclinal conformation, nearly orthogonal to the pyrimidine ring, with a dihedral angle between the chloro-ethyl side chain and the pyrimidine ring of 88.5?(1)°. Weak inter-molecular C-H?N and C-H?Cl hydrogen bonds along with ?-? inter-actions between the pyrimidine and pyridine rings [centroid-centroid distance is 3.538?(2)?Å] form a three-dimensional network. The crystal is a racemic twin with a 0.68?(12):0.32?(12) domain ratio. MOPAC AM1 and density functional theory (DFT) theoretical calculations at the B3-LYP/6-311+G(d,p) level support these observations.

| S-EPMC2977208 | biostudies-literature

Spiro-[cyclo-pentane-1,2'(1'H)-pyrido[2,3-d]pyrimidin]-4'(3'H)-one.

Project description:The title compound, C(11)H(13)N(2)O, was obtained by cyclo-condensation of 2-amino-pyridine-3-carbonitrile with cyclo-penta-none. The mol-ecule is built up from two fused six-membered rings and one five-membered ring linked through a spiro C atom. Both the pyrimidine and the cyclo-pentane rings adopt envelope conformations. In the crystal structure, mol-ecules are linked by inter-molecular N-H⋯O hydrogen bonds.

| S-EPMC3008029 | biostudies-literature

A simple and convenient one-pot synthesis of substituted isoindolin-1-ones via lithiation, substitution and cyclization of N'-benzyl-N,N-dimethylureas.

Project description:Lithiation of N'-benzyl-N,N-dimethylurea and its substituted derivatives with t-BuLi (3.3 equiv) in anhydrous THF at 0 °C followed by reaction with various electrophiles afforded a range of 3-substituted isoindolin-1-ones in high yields.

| S-EPMC3182431 | biostudies-literature

1,2-Diphenyl-2-[4-(4-pyridyl)benzyl-idene-hydrazono]ethan-1-one.

Project description:In the title compound, C(26)H(19)N(3)O, the dimethyl-ene hydrazine (-C=N-N=C-) unit is approximately planar, the torsion angle around the N-N bond being 162.2?(6)°. The phenyl and benzoyl-phenyl rings at one end of the hydrazine unit are aligned at angles of 9.5?(5) and 88.5?(4)°, respectively, with respect to the hydrazine unit, whereas the benzene ring at the other end is twisted by an angle of 14.4?(4)°. In the crystal structure, mol-ecules are linked into centrosymmetric dimers by inter-molecular C-H?O hydrogen bonds. The monoclinic crystal under investigation shows pseudo-merohedral twinning with twin fractions of 0.63 and 0.37.

| S-EPMC2977415 | biostudies-literature

One-Pot Synthesis of Benzo[4,5]imidazo[1,2-a]pyrimidin-2-ones Using a Hybrid Catalyst Supported on Magnetic Nanoparticles in Green Solvents.

Project description:The conversion of soluble polyoxometalate into insoluble polyoxometalate is considered to be one of the major challenges in synthetic organic chemistry. Here, polyoxometalate was bonded to the salt part of an organic branch immobilized on the silica-coated Fe3 O4 nanoparticle and characterized using various techniques. The fabricated complex was used as a heterogeneous catalyst in a novel one-pot reaction for synthesis of benzo[4,5]imidazo[1,2-a]pyrimidin-2-ones using aromatic amines, dimethyl acetylenedicarboxylate (DMAD), derivatives of benzaldehyde and 2-aminobenzimidazole in water/ethanol as a green solvent. 21 derivatives of benzo[4,5]imidazo[1,2-a]pyrimidin-2-one were synthesized by this method and fully characterized. The high stability of the catalyst showed that it can be reused for 6 times without decreasing in activity. The combination of new synthetic method, new ferromagnetic heterogeneous nano-catalyst, green solvent and simple separation method were presented in this work.

| S-EPMC8340068 | biostudies-literature

3-Benzyl-6-isopropyl-5-phen-oxy-3H-1,2,3-triazolo[4,5-d]pyrimidin-7(6H)-one.

Project description:In the title compound, C(20)H(19)N(5)O(2), all atoms of the 1,2,3-triazolo[4,5-d]pyrimidine ring system are essentially coplanar [maximum deviation = 0.015?(2)?Å], indicating the existence of a conjugate system in which each carbon and nitrogen atom is sp(2) hybridized and ten ? electrons (three from carbon atoms and seven from nitrogen atoms) constitute an aromatic heterocycle. The ring system forms dihedral angles of 68.37?(10) and 71.57?(9)° with the phenyl rings. The crystal packing is stabilized by van der Waals inter-actions and intermolecular C-H?? interactions.

| S-EPMC2971348 | biostudies-literature

Hexafluoroisopropyl alcohol mediated synthesis of 2,3-dihydro-4H-pyrido[1,2-a]pyrimidin-4-ones.

Project description:An efficient synthesis of novel 2,3-dihydro-4H-pyrido[1,2-a]pyrimidin-4-ones has been reported. Inexpensive and readily available substrates, environmentally benign reaction condition, and product formation up to quantitative yield are the key features of this methodology. Products are formed by the aza-Michael addition followed by intramolecular acyl substitution in a domino process. The polar nature and strong hydrogen bond donor capability of 1,1,1,3,3,3-hexafluoropropan-2-ol is pivotal in this cascade protocol.

| S-EPMC5090868 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data