Synthesis of 3-(6-Azauracil-5-yl)anthranilic Acid and Its Application to the Preparation of Other 1,2,4-Triazine Derivatives

1996 ◽  
Vol 61 (6) ◽  
pp. 941-945 ◽  
Author(s):  
Jan Hlaváč ◽  
Jan Slouka

The title compound was synthesized by alkaline recyclization of isatin-7-carboxylic acid semicarbazone and used for the preparation of 3-oxo-2,3-dihydro-5H-1,2,4-triazino[5,6-b]indol-6-carboxylic acid (8) and 3-oxo-2,3,4,6-tetrahydro-1,2,4-triazino[5,6-c]cinnoline-7-carboxylic acid (9).

2006 ◽  
Vol 62 (7) ◽  
pp. o2751-o2752 ◽  
Author(s):  
Ting Sun ◽  
Jian-Ping Ma ◽  
Ru-Qi Huang ◽  
Yu-Bin Dong

In the title compound, C10H7N3O4·H2O, one carboxyl group is deprotonated and the pyridyl group is protonated. The inner salt molecule has a planar structure, apart from the carboxylic acid group, which is tilted from the imidazole plane by a small dihedral angle of 7.3 (3)°.


2009 ◽  
Vol 65 (6) ◽  
pp. o1429-o1429
Author(s):  
Zhen-Dong Zhao ◽  
Yu-Xiang Chen ◽  
Yu-Min Wang ◽  
Liang-Wu Bi

The title compound, also known as isopimaric acid, C20H30O2, was isolated from slash pine rosin. There are two unique molecules in the unit cell. The two cyclohexane rings have classical chair conformations. The cyclohexene ring represents a semi-chair. The molecular conformation is stabilized by weak intramolecular C—H...O hydrogen-bonding interactions. The molecules are dimerized through their carboxyl groups by O—H...O hydrogen bonds, formingR22(8) rings.


2014 ◽  
Vol 70 (6) ◽  
pp. o696-o697
Author(s):  
Md. Lutfor Rahman ◽  
H. T. Srinivasa ◽  
Mashitah Mohd. Yusoff ◽  
Huey Chong Kwong ◽  
Ching Kheng Quah

The asymmetric unit of the title compound, C17H18O3, comprises three independent molecules with similar geometries. In each molecule, the carbonyl group is twisted away from the napthalene ring system, making dihedral angles of 1.0 (2), 1.05 (19)° and 1.5 (2)°. The butene group in all three molecules are disordered over two sets of sites, with a refined occupancy ratio of 0.664 (6):0.336 (6). In the crystal, molecules are oriented with respect to their carbonyl groups, forming head-to-head dimersviaO—H...O hydrogen bonds. Adjacent dimers are further interconnected by C—H...O hydrogen bonds into chains along thea-axis direction. The crystal structure is further stabilized by weak C—H...π interactions.


1968 ◽  
Vol 23 (8) ◽  
pp. 1072-1075 ◽  
Author(s):  
D. Gröger ◽  
S. Johne

The biosynthesis of some alkaloids of Glycosmis arborea (Roxb.) DC has been studied. Using labelled compounds it has been shown that the chinazolone-alkaloid arborine is derived from phenylalanine and anthranilic acid. After feeding anthranilic acid-T the isolated acridone-alkaloid arborinine was degradated to 1-methyl-4-chinolon-3-carboxylic acid. This compound had the same specific radioactivity as arborinine. So one might conclude anthranilic acid is a precursor of ring A of the acridine-alkaloids.Die Familie der Rutaceen umfaßt etwa 150 Genera, die vorwiegend in den Tropen und Subtropen verbreitet sind. In rund 40 Gattungen, besonders der Unterfamilien Rutoideae und Toddalioideae, sind bisher Alkaloide nachgewiesen worden. Die Alkaloide gehören den unterschiedlichsten Struktur-Typen an. Die am häufigsten vertretene Gruppe sind die Furochinoline. Das Vorkommen dieses Alkaloid-Types sowie der Acridine, Imidazol-Alkaloide und Indolochinazoline scheint auf die Rutaceen beschränkt zu sein.


Author(s):  
Noureddine Beghidja ◽  
Samir Benayache ◽  
Fadila Benayache ◽  
David W. Knight ◽  
Benson M. Kariuki

In the title compound, C15H22O2, both five-membered rings display an envelope conformation whereas the six-membered ring displays a chair conformation. In the crystal, pairs of O—H...O hydrogen bonds between carboxylic groups link molecules, related by a twofold rotation axis, into supramolecular dimers.


2007 ◽  
Vol 63 (11) ◽  
pp. o4474-o4474 ◽  
Author(s):  
Guanghua Zhou ◽  
Yue An ◽  
Jing Han ◽  
Maofa Ge ◽  
Yongheng Xing

The title compound, C11H10N2O2, was prepared by the esterfication of 5-phenyl-1H-pyrazole-3-carboxylic acid with methanol. The phenyl ring is rotated out of the pyrazole plane, forming a dihedral angle of 6.4 (1)°. The crystal structure is stabilized by intermolecular aromatic π–π interactions [with a centroid–centroid distance of 3.862 (3) Å between the pyrazole ring and the benzene ring of a neighboring molecule], and by three different types of hydrogen bond (N—H...N, N—H...O and C—H...O).


2015 ◽  
Vol 71 (5) ◽  
pp. o323-o323 ◽  
Author(s):  
Tim Peppel ◽  
Marcel Sonneck ◽  
Anke Spannenberg ◽  
Sebastian Wohlrab

The crystal structure of the title compound, C6H10O2, an α,β-unsaturated carboxylic acid, displays carboxylic acid inversion dimers linked by pairs of O—H...O hydrogen bonds. The packing is characterized by layers of acid dimers. All the non-H atoms of the (E)-hex-2-enoic acid molecule lie almost in the same plane (r.m.s. deviation for the non-H atoms = 0.018 Å).


2014 ◽  
Vol 70 (12) ◽  
pp. 499-502
Author(s):  
Md. Lutfor Rahman ◽  
Mashitah Mohd. Yusoff ◽  
Jamil Ismail ◽  
Huey Chong Kwong ◽  
Ching Kheng Quah

The title compound, C16H14N2O3, has anEconformation about the azobenzene [—N=N– = 1.2481 (16) Å] linkage. The benzene rings are almost coplanar [dihedral angle = 1.36 (7)°]. The O atoms of the carboxylic acid group are disordered over two sets of sites and were refined with an occupancy ratio of 0.5:0.5. The two disordered components of the carboxylic acid group make dihedral angles of 1.5 (14) and 3.8 (12)° with the benzene ring to which they are attached. In the crystal, molecules are linkedviapairs of O—H...O hydrogen bonds, forming inversion dimers. The dimers are connectedviaC—H...O hydrogen bonds, forming ribbons lying parallel to [120]. These ribbons are linkedviaC—H...π interactions, forming slabs parallel to (001).


2009 ◽  
Vol 65 (6) ◽  
pp. o1192-o1192 ◽  
Author(s):  
Piotr Kuś ◽  
Marcin Rojkiewicz ◽  
Grzegorz Zięba ◽  
Monika Witoszek ◽  
Peter G. Jones

In the title compound, C10H16O6, the five-membered ring has an envelope conformation. The packing involves hydrogen-bonded carboxylic acid inversion dimers and three C—H...O interactions.


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