Synthesis and structure of aziridine-2-carboxylic acid derivatives with asymmetric substituents attached to the nitrogen atom

1982 ◽  
Vol 18 (11) ◽  
pp. 1159-1164
Author(s):  
A. V. Eremeev ◽  
F. D. Polyak ◽  
A. F. Mishnev ◽  
Ya. Ya. Bleidelis ◽  
�. �. Liepin'sh ◽  
...  
2019 ◽  
Vol 138 (4) ◽  
pp. 2813-2837 ◽  
Author(s):  
G. Świderski ◽  
R. Świsłocka ◽  
R. Łyszczek ◽  
S. Wojtulewski ◽  
M. Samsonowicz ◽  
...  

Abstract The new 3d metal complexes of pyrimidine-2-carboxylic (2PCA) and pyrimidine-5-carboxylic (5PCA) acids were synthesized and characterized using thermal analysis (TG–DSC, TG–FTIR), X-ray, spectroscopic (IR, Raman) methods and theoretical (DFT) studies. In the complexes of pyrimidine-2-carboxylic acid of the general formula M(2PCA)2·xH2O (where 2PCA-pyrimidine-2-carboxylate; M = Mn(II), Co(II), Ni(II), Cu(II) and Zn; x = 0 for Mn and Cu; x = 2 for Co, Ni and Zn) coordination of metal ions occurs through nitrogen atom from pyrimidine ring and carboxylate oxygen atom. The complexes of pyrimidine-5-carboxylic acid of the general formula M(5PCA)2·xH2O (where 5PCA—pyrimidine-5-carboxylate; M = Mn(II), Co(II), Ni(II), Cu(II) and Zn; x = 6 for Cu and 4 for remaining complexes) were obtained as monomeric isostructural compounds. Coordination of metal centers occurs through two nitrogen atom from different pyrimidine-5-carboxylate ligand and four oxygen atoms from water molecules. The IR and Raman spectra of free acids as well as obtained metal(II) complexes were described in detail. Aromaticity (HOMA, EN, GEO and I6) of complexes was determined and discussed. The investigated compounds decompose in air in two main stages connected with dehydration and decomposition/burning of anhydrous compounds to the suitable metal oxides. Thermal decomposition in nitrogen leads to the evolution of water, carbon oxides, ammonia and pyrimidine molecules.


2017 ◽  
Vol 13 ◽  
pp. 579-588 ◽  
Author(s):  
Jan Szabo ◽  
Julian Greiner ◽  
Gerhard Maas

Depending on the reaction conditions, N,N’,N’’-tris(benzylamino)guanidinium salts can react with carboxylic acid chlorides to form either symmetrical N,N’,N’’-tris(N-acyl-N-benzylamido)guanidines 6 or mesoionic 4-amino-1,2,4-triazolium-3-hydrazinides 7. The latter were converted into 1,2,4-triazolium salts by protonation or methylation at the hydrazinide nitrogen atom. Neutral 1,2,4-triazoles 10 were obtained by catalytic hydrogenation of an N-benzyl derivative. Crystal structure analyses of a 4-benzylamino-1,2,4-triazolium-3-hydrazinide and of two derived 1,2,4-triazolium salts are presented.


1975 ◽  
Vol 24 (4) ◽  
pp. 246-252
Author(s):  
Hirohumi HIRATA ◽  
Ken-ichi IMAEDA ◽  
Hiroshi TANAKA ◽  
Kazuo FUKUZUMI

2016 ◽  
Vol 72 (10) ◽  
pp. 1429-1433
Author(s):  
Dmitry S. Poplevin ◽  
Fedor I. Zubkov ◽  
Pavel V. Dorovatovskii ◽  
Yan V. Zubavichus ◽  
Victor N. Khrustalev

The isomeric title compounds, C12H13NO4(Ia) and C12H13NO4(IIa), the products of an usual thermal C6-epimerization of 5-oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid, represent the two different diastereomers and have very similar molecular geometries. The molecules of both compounds comprise a fused tetracyclic system containing four five-membered rings (pyrrolidine, pyrrolidinone, dihydrofuran and tetrahydrofuran), all of which adopt the usual envelope conformations. The dihedral angle between the basal planes of the pyrrolidine and pyrrolidinone rings are 14.3 (2) and 16.50 (11)°, respectively, for (Ia) and (IIa). The nitrogen atom has a slightly pyramidalized geometry [bond-angle sum = 355.9 and 355.3°, for (Ia) and (IIa)], respectively. In the crystal of (Ia), molecules form zigzag-like hydrogen-bonded chains along [010] through strong O—H...O hydrogen bonds and are further linked by weak C—H...O hydrogen bonds into complex two-tier layers parallel to (100). Unlike (Ia), the crystal of (IIa) contains centrosymmetric cyclic hydrogen-bonded dimers [graph setR22(14)], formed through strong O—H...O hydrogen bonds and are further linked by weak C—H...O hydrogen bonds into ribbons extending across [101].


1983 ◽  
Vol 14 (17) ◽  
Author(s):  
A. V. EREMEEV ◽  
F. D. POLYAK ◽  
A. F. MISHNEV ◽  
YA. YA. BLEIDELIS ◽  
E. E. LIEPINSH' ◽  
...  

2003 ◽  
Vol 56 (7) ◽  
pp. 707 ◽  
Author(s):  
Graham Smith ◽  
Urs D. Wermuth ◽  
Peter C. Healy ◽  
Jonathan M. White

The crystal structures of the proton-transfer compounds of 3,5-dinitrosalicylic acid (dnsa) with a series of common monocyclic heteroaromatic amines (pyridine, 4-cyanopyridine, pyridine-4-carboxylic acid, 2,6-diaminopyridine, and 2-aminopyrimidine) have been determined and the hydrogen-bonding associations in each analyzed. The compounds are the adduct [(C5H6N)+(dnsa)–· (dnsa)] (1), the 1 : 1 salts [(C6H5N2)+(dnsa)–] (2), [(C6H6NO2)+(dnsa)–] (3), [(C5H8N3)+(dnsa)–] (4), and the 2 : 2 ethanol hemi-solvate [2(C4H6N3)+·2(dnsa)–· 0.5(EtOH)] (5). With all compounds, protonation of the hetero-nitrogen atom occurs with subsequent hydrogen bonding to the oxygen atoms of the functional groups of the dnsa anions, resulting in the formation of relatively simple linear or chain polymer associations. Compound (1) represents a rare example of other than a 1 : 1 association, and the first example of a 2 : 1 (dnsa/amine) type, with the unusual presence of an additional adduct molecule of dnsa in the structure.


1969 ◽  
Vol 21 (02) ◽  
pp. 294-303 ◽  
Author(s):  
H Mihara ◽  
T Fujii ◽  
S Okamoto

SummaryBlood was injected into the brains of dogs to produce artificial haematomas, and paraffin injected to produce intracerebral paraffin masses. Cerebrospinal fluid (CSF) and peripheral blood samples were withdrawn at regular intervals and their fibrinolytic activities estimated by the fibrin plate method. Trans-form aminomethylcyclohexane-carboxylic acid (t-AMCHA) was administered to some individuals. Genera] relationships were found between changes in CSF fibrinolytic activity, area of tissue damage and survival time. t-AMCHA was clearly beneficial to those animals given a programme of administration. Tissue activator was extracted from the brain tissue after death or sacrifice for haematoma examination. The possible role of tissue activator in relation to haematoma development, and clinical implications of the results, are discussed.


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