Metal halide coordination compounds with quinazolin-4(3)-one.

Three coordination compounds of quinazolin-4(3)-one (; CHNO) with divalent group 12 halides are reported. In all complexes, coordination occurs the nitro-gen atom to the quinazolinone carbonyl group. In the two chain polymers with composition [ ()], .

Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzyl-sulfan-yl)-5-[4-(di-methyl-amino)-phen-yl]-1,3,4-oxa-diazole and 2-[(2-chloro-6-fluoro-benz-yl)sulfan-yl]-5-[4-(di-methyl-amino)-phen-yl]-1,3,4-oxa-diazole.

The title compounds were synthesized by alkyl-ation of 5-[(4-di-methyl-amino)-phen-yl]-1,3,4-oxa-diazole-2-thiol with benzyl chloride or 2-chloro-6-fluoro-benzyl chloride in the presence of potassium carbonate. The yields of 2-(benzyl-sulfan-yl)-5-[4-(di-methyl-amino)-phen-yl]-1,3,4-oxa-diazole, CHNOS (I), and 2-[(2-chloro-6-fluoro-benz-yl)sulfan-yl]-5-[4-(di-methyl-amino)-phen-yl]-1,3,4-oxa-diazole, CHClFNOS (II), were 96 and 92%, respectively. In the crystal structures of (I) and (II), C-H⋯π inter-actions are observed between neighboring mol-ecules.

Syntheses, crystal structures and Hirshfeld surface analyses of -aryl-sulfonyl derivatives of cytisine.

By aryl-sulfonyl-ation of cytisine in the presence of tri-ethyl-amine, three new compounds have been obtained in good yields: (7,9)--[(4-ethyl-phen-yl)sulfon-yl]cytisine, CHNOS () {systematic name: (1,5)-3-[(4-ethyl-phen-yl)sulfon-yl]-1,2,3,4,5,6-hexa-hydro-8-1,5-methano-pyrido[1,2-][1,5]diazo-cin-8-one}, (7,9)--[(4-chloro-phen-yl)sulfon-yl]cytisine, CHClNOS () {systematic name: (1,5)-3-[(4-chloro-phen-yl)sulfon-yl]-1,2,3,4,5,6-hexa-hydro-8-1,5-methano-pyrido[1,2-][1,5]diazo-cin-8-one} and (7,9)--[(3-nitro-phen-yl)sulfon-yl]cytisine, CHNOS () {systematic name: (1,5)-3-[(3-nitro-phen-yl)sulfon-yl]-1,2,3,4,5,6-hexa-hydro-8-1,5-methano-pyrido[1,2-][1,5]diazo-cin-8-one}. The crystal structures of the compounds were determined on the basis of single-crystal X-ray diffraction data. The crystal structures of ()-() are distinguished by the arrangement of two fragments of the mol-ecule around the sulfonyl site.

Crystal structures of 6-nitro-quinazolin-4(3)-one, 6-amino-quinazolin-4(3)-one and 4-amino-quinazoline hemi-hydro-chloride dihydrate.

The title compounds, 6-nitro-quinazolin-4(3)-one (CHNO; ), 6-amino-quinazolin-4(3)-one (CHNO; ) and 4-amino-quinazolin-1-ium chloride-4-amino-quinazoline-water (1/1/2), (CHN ·Cl·CHN·2HO; ) were synthesized and their structures were determined by single-crystal X-ray analysis. In the crystals of and , the quinazoline mol-ecules form hydrogen-bonded dimers N-H⋯O inter-actions. The dimers are connected by weak inter-molecular C-H⋯N and C-H⋯O hydrogen bonds, forming a layered structure in the case of .

Withanolides from L.

The compounds (17,20,22,24,25)-5β,6β:20,24-diep-oxy-4β,25-dihy-droxy-1-oxowith-2-en-26,22-olide and (20,22)-5α,14α,20-Trihy-droxy-1-oxo-6α,7α-ep-oxy-witha-2-enolide were isolated from a chloro-form extract of the aerial parts of L. (Solanaceae). Two products were isolated from the chromatographic separation extract.

Crystal structures of 2-amino-2-oxoethyl 4-bromo-benzoate, 2-amino-2-oxoethyl 4-nitro-benzoate and 2-amino-2-oxoethyl 4-amino-benzoate monohydrate.

The title mol-ecules were synthesized by the reaction of 4-substituted sodium benzoates with chloro-acetic acid amide in the presence of di-methyl-formamide. The yields of 2-amino-2-oxoethyl 4-bromo-benzoate, CHBrNO, , 2-amino-2-oxoethyl 4-nitro-benzoate, CHNO, , and 2-amino-2-oxoethyl 4-amino-benzoate monohydrate, CHNO·HO, , are 86, 78 and 88%, respectively. The low yield of is explained by the reduced reactivity of the mol-ecule in a nucleophilic exchange reaction because of the negative induction and negative mesomeric effects of the nitro group on the benzene ring.

Unusual formation of ()-11-(amino-methyl-ene)-8,9,10,11-tetra-hydro-pyrido[2',3':4,5]pyrimido[1,2-]azepin-5(7)-one and its crystal structure.

Selective C-formyl-ation of 8,9,10,11-tetra-hydro-pyrido[2',3':4,5]pyrimido[1,2-]-azepin-5(7)-one has been studied for the first time. It was revealed that formyl-ation proceeds by the formation of an inter-mediate salt, which due to the re-amination process on treatment with aqueous ammonia transformed into the corresponding ()-11-(amino-methyl-ene)-8,9,10,11-tetra-hydro-pyrido[2',3':4,5]-pyrimido[1,2-]azepin-5(7)-one, CHNO, as an -isomer. Formyl-ation was carried out by Vilsmeier-Haack reagent and the structure of the synthesized compound was confirmed by X-ray structural analysis, spectroscopic and LC-MS methods.

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.

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.

Crystal structure of 2,3-dimeth-oxy-5,6,7,8,13,13a-hexa-hydro-6a,8-di-aza-indeno-[2,1-b]phenanthrene methanol monosolvate.

The asymmetric unit of the title solvate, C21H22N2O2·CH3OH, contains one methanol solvent mol-ecule and one mol-ecule of the heterocycle that is built up by the fusion of four six-membered rings A, C, D, E and one five-membered ring B. The indole moiety (rings A and B) is essentially planar, with an r.m.

Crystal structure of anagyrine perchlorate.

The title mol-ecular salt, C15H21N2O(+)·ClO4 (-), crystallizes with four cations (A, B, C and D) and four anions in the chiral unit cell (space group P21). The alkaloid was isolated from the aerial parts of Genista Hispanica collected in the Samarkand region of Uzbekistan. Each cation is protonated at the N atom that bridges the alkaloid rings C and D.

2,3-Di-methyl-quinazolin-4(3H)-one.

The non-H atoms of the title mol-ecule, C10H10N2O, are essentially coplanar, with a maximum deviation of 0.046 (4) Å for the O atom. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming chains along [010].

N-(5-Benzyl-sulfanyl-1,3,4-thia-diazol-2-yl)-2-(piperidin-1-yl)acetamide.

The title compound, C16H20N4OS2, was synthesized by the reaction of 2-benzyl-sulfanyl-5-chloro-acetamido-1,3,4-thia-diazole and piperidine in a 1:2 ratio. The planes of the acetamide and 1,3,4-thia-diazole units are twisted by 10.8 (4)°.

[2-(3,4-Di-meth-oxy-phen-yl)eth-yl](3-{N-[2-(3,4-di-meth-oxy-phen-yl)eth-yl]carbamo-yl}prop-yl)aza-nium chloride dihydrate.

The asymmetric unit of the title hydrated salt, C24H35N2O5 (+)·Cl(-)·2H2O, contains one organic cation that has its protonation site at the amine function, one chloride anion and two lattice water mol-ecules. In the crystal, one pair of lattice water mol-ecules and two chloride anions form a four-membered centrosymmetric hydrogen-bond cycle. In addition, O-H⋯O, N-H⋯O and N-H⋯Cl hydrogen bonds involving the N-H groups, the water mol-ecules and the C=O group are observed.

2,3-Tri-methyl-ene-7,8-di-hydro-pyrrolo-[1,2-a]thieno[2,3-d]pyrimidin-4(6H)-one.

The title mol-ecule, C12H12N2OS, is planar, with an r.m.s.

(-)-Norfluoro-curarine ethanol monosolvate.

The title compound, C19H20N2O·C2H5OH, is an ethanol solvate of an indol alkaloid which was extracted from the plant Vinca erecta. The fused piperidine ring adopts an approximate boat conformation and the pyrrolidine ring an envelope conformation with one of the methyl-ene C atoms at the flap. An intra-molecular N-H⋯O hydrogen bond forms an S6 ring motif.

3-Methyl-2-(3,3,3-tri-chloro-2-hy-droxy-prop-yl)quinazolin-4(3H)-one.

The title mol-ecule, C12H11Cl3N2O2, contains planar quinazolin-4(3H)-one (r.m.s.

5,7-Dihy-droxy-2-(3-hy-droxy-4,5-dimeth-oxy-phen-yl)-6-meth-oxy-4H-chromen-4-one.

The title compound, C18H16O8, was isolated from the plant Artemisia baldshuanica Krasch et Zarp. The mol-ecule is approximately planar, with the exception of the terminal methyl groups, the C atoms of which devitate from their attached ring planes by 1.243 (5) and 1.

2,3-Dihydro-pyrrolo-[2,1-b]quinazoline-9(1H)-thione.

In the crystal, mol-ecules of the title compound, C(11)H(10)N(2)S, are connected by C-H⋯N inter-actions around threefold axes. Furthermore, they form stacks along the c axis showing π-π inter-actions between pyrimidine rings [centroid-centroid distance = 3.721 (1) Å].

(4-Nitrophenyl)(1,2,3,9-tetrahydro-pyrrolo[2,1-b]quinazolin-3-yl)methanol monohydrate.

In the crystal structure of the title compound, C(18)H(17)N(3)O(3)·H(2)O, the mol-ecules are linked by O-H⋯O and O-H⋯N hydrogen bonds, resulting in a chain along the a axis. The crystal structure is stabilized by weak inter-molecular C-H⋯π (ring) hydrogen bonds and aromatic π⋯π stacking inter-actions [centroid-centroid distance = 3.902 (1) Å] between the pyrimidino rings of the quinazoline system.

2-Methyl-4-oxo-6,7,8,9-tetrahydro-thieno[2',3':4,5]pyrimidino-[1,2-a]pyridine-3-carboxylic acid.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(12)H(12)N(2)O(3)S. With the exception of the methyl-ene groups, a mean plane fitted through all non-H atoms of each mol-ecule has an r.m.

(E)-3-[4-(Dimethyl-amino)-benzyl-idene]-2,3-di-hydro-1H,9H-pyrrolo-[2,1-b]quinazolin-9-one.

The title compound, C(20)H(19)N(3)O, was obtained by condensation of 2,3-dihydro-1H,9H-pyrrolo-[2,1-b]quinazolin-9-one (alkaloid de-oxy-vasicinone, isolated from Peganum Harmala) with 4-(dimethyl-amino)-benzaldehyde in the presence of sodium methoxide. The 2,3-dihydro-1H,9H-pyrrolo-[2,1-b]quinazolin-9-one part of the mol-ecule is roughly planar (r.m.

11-(2-Oxopyrrolidin-1-ylmeth-yl)-1,2,3,4,5,6,11,11a-octa-hydro-pyrido[2,1-b]quinazolin-6-one dihydrate.

In the crystal structure of the title compound, C(17)H(21)N(3)O(2)·2H(2)O, water mol-ecules are mutually O-H⋯O hydrogen bonded and form infinite chains propagating along the b axis. Neighboring chains are linked by the quinazoline mol-ecules by means of O-H⋯O=C hydrogen bonds, forming a two-dimensional network.

9-Furfuryl-idene-2,3-dimethyl-6,7,8,9-tetrahydro-4H--thieno[2',3':4,5]pyrimidino[1,2-a]pyridin-4-one.

The title compound, C(17)H(16)N(2)O(2)S, was obtained by condensation of 2,3-dimethyl-thieno[2',3':4,5]pyrimidino[1,2-a]pyridin-4-one with furfural in the presence of sodium hydroxide. One of the methyl-ene groups of the tetra-hydro-pyrido ring is disordered over two positions in a 0.87 (1):0.

(E)-3-Propoxymethyl-idene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one monohydrate.

The title compound, C(15)H(16)N(2)O(2)·H(2)O, was synthesized via the alkyl-ation of 3-hydroxy-methyl-idene-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one with n-propyl iodide in the presence of sodium hydroxide. The organic mol-ecule and the water mol-ecule both lie on a crystallographic mirror plane. In the crystal structure, inter-molecular O-H⋯O and O-H⋯N hydrogen bonds link the components into extended chains along [100].

6,7,8,9,10,11-Hexahydro-13H-azocino[2,1-b]quinazolin-13-one.

The title compound, C(14)H(16)N(2)O, is a synthetic analogue of quinazolone alkaloids with pyrrilo, pyrido and azopino rings. The quinazolinic part of the mol-ecule is generally planar within 0.037 (3) Å; the eight-membered ring exhibits an inter-mediate conformation between the chair and boat forms as it is typical for cyclo-octene rings.