Synthesis of Some New 2‐Oxo‐N‐[(10H‐phenothiazin‐10‐yl)alkyl] Derivatives of Azetidine‐1‐carboxamides

The synthesis of a new series of 4‐aryl‐3‐chloro‐2‐oxo‐N‐[3‐(10H‐phenothiazin‐10‐yl)propyl]azetidine‐1‐carboxamides, 4a – 4m , is described. Phenothiazine on reaction with Cl(CH₂)₃Br at room temperature gave 10‐(3‐chloropropyl)‐10H‐phenothiazine ( 1 ), and the latter reacted with urea to yield 1‐[3‐(10H‐phenothiazin‐10‐yl)propyl]urea ( 2 ). Further reaction of 2 with several substituted aromatic aldehydes led to N‐(arylmethylidene)‐N′‐[3‐(phenothiazin‐10‐yl)propyl]ureas 3a – 3m , which, on treatment with ClCH₂COCl in the presence of Et₃N, furnished the desired racemic trans‐2‐oxoazetidin‐1‐carboxamide derivatives 4a – 4m . The structures of all new compounds were confirmed by IR, and ¹H‐ and ¹³C‐NMR spectroscopy, FAB mass spectrometry, and chemical methods.     

The conversion of a pyrrole trimer derivative into a 4,5,6,7‐tetra­hydro‐4‐­(pyrrol‐2‐yl)indol‐7‐yl­tosyl­aminoindole

Vilsmeier formyl­ation of trans‐1‐(4‐methyl­phenyl­sulfonyl)‐2,5‐bis(pyrrol‐2‐yl)­pyrrolidine leads to cleavage of the central ring then a reclosure resulting in the formation of trans‐N‐[2‐formyl‐4‐(5‐formyl­pyrrol‐2‐yl)‐4,5,6,7‐tetra­hydro­indol‐7‐yl]­toluene­sulfon­amide, C₂₁H₂₁N₃O₄S.     

Syntheses and properties of benzodipyrrinones

2,3‐Benzannelated dipyrrinone analogs ( 1 and 2 ) of xanthobilirubic acid ( 3 ) are prepared by base‐catalyzed condensation of isoindolinone ( 5 ) and indolin‐2‐one ( 6 ) respectively, with methyl 3‐(2‐formyl‐3,5‐dimethyl‐1H‐pyrrol‐4‐yl)propanoate ( 4 ). Nuclear Overhauser effect H‐nmr studies indicate that both 1 and 2 adopt preferentially a syn‐Z configuration. The former forms a hydrogen‐bonded homodimer in nonpolar solvents; the latter is intramolecularly hydrogen bonded.     

Synthesis and Structural Characterization of Metal Complexes of 2‐Formylpyrrole‐4N‐ethylthiosemicarbazone (4 EL1) and 2‐Acetylpyrrole‐4N‐ethylthiosemicarbazone (4 EL2)

The reactions of ⁴N‐ethyl‐2‐[1‐(pyrrol‐2‐yl)methylidene(hydrazine carbothioamide ( 4 EL₁ ) and ⁴N‐ethyl‐2[1‐(pyrrol‐2‐yl)ethylidene(hydrazine carbothioamide ( 4 EL₂ ) with Group 12 metal halides afforded complexes of types [M(L)₂X₂] (M = Zn, Cd; L = 4 EL₁, 4 EL₂; X = Cl, Br, I; 1 – 6 , 14 – 19 ) and [M(L)X₂] (M = Hg; L = 4 EL₁, 4 EL₂; X = Cl, Br, I; 7 – 9 , 20 – 22 ). In addition, reaction of 4 EL₁ with salts of Cu^II, Ni^II, Pd^II and Pt^II afforded compounds of type [M(4 EL₁–H)₂] ( 10 – 13 ). The new compounds were characterized by elemental analysis, FAB mass spectrometry, IR and electronic spectroscopy and, for sufficiently soluble compounds, ¹H, ¹³C and, when appropriate, ¹¹³Cd or ¹⁹⁹Hg NMR spectrometry. The spectral data suggest that in their complexes with Group 12 metal cations, both thiosemicarbazones are neutral and S‐monodentate; and for [Zn(4 EL₁)₂I₂] ( 3 ), [Cd(4 EL₁)₂Br₂] ( 5 ) and [Hg(4 EL₁)Cl₂]₂ ( 7 ) this was confirmed by X‐ray diffractometry. By contrast, in its complexes with Cu^II and Group 10 metal cations, 4 EL₁ is monodeprotonated and S,N‐bidentate, as was confirmed by X‐ray diffractometry for [Ni(4 EL₁–H)₂] ( 11 ) and [Pd(4 EL₁–H)₂] ( 12 ).     

Chemical Constituents from the Fermented Mycelia of the Medicinal Fungus Xylaria nigripes

Nineteen compounds mainly including pyrrole‐containing alkaloids and phytosterols were isolated from the EtOH extract of the fermented mycelia of Xylaria nigripes, a precious medicinal fungus known as Wuling Shen in Chinese. On the basis of spectroscopic methods, the structures of the new naturally occurring compounds were determined to be (4S)‐3,4‐dihydro‐4‐(4‐hydroxybenzyl)‐3‐oxo‐1H‐pyrrolo[2,1‐c][1,4]oxazine‐6‐carbaldehyde ( 1 ), methyl (2S)‐2‐[2‐formyl‐5‐(hydroxymethyl)‐1H‐pyrrol‐1‐yl]‐3‐(4‐hydroxyphenyl)propanoate ( 2 ), and 3‐{4‐[(2R)‐(2,3‐dihydroxy‐3‐methylbutoxy]phenyl}‐7‐hydroxy‐4H‐chromen‐4‐one ( 3 ), respectively. The absolute configurations of 1 and 2 were deduced by the observed Cotton effects in their circular dichroism (CD) spectra, whereas that of the 1,2‐diol moiety in 3 was determined using the Snatzke's method. Their biological activities such as neuroprotective, anti‐neuroinflammatory, and cytotoxic properties were also reported.     

Isomeric 3‐ and 4‐chloro‐N‐[1‐(1H‐pyrrol‐2‐yl)ethylidene]aniline

The title isomers, namely 3‐chloro‐N‐[1‐(1H‐pyrrol‐2‐yl)ethylidene]aniline, (I), and 4‐chloro‐N‐[1‐(1H‐pyrrol‐2‐yl)ethylidene]aniline, (II), both C₁₂H₁₁ClN₂, differ in the position of the chlorine substitution. Both compounds have the basic iminopyrrole structure, which shows a planar backbone with similar features. The dihedral angle formed by the planes of the pyrrole and benzene rings is 75.65 (7)° for (I) and 86.56 (8)° for (II). The H atom bound to the pyrrole N atom is positionally disordered and partial protonation occurs at the imino N atom in (I), while this phenomenon is absent from the structure of (II). Packing interactions for both compounds include intermolecular N—H...N hydrogen bonds and C—H...π interactions, forming centrosymmetric dimers for both (I) and (II).     

A concise and efficient synthesis of amino‐substituted (1H‐benzo[d]imidazol‐1‐yl)pyrimidine hybrids: synthetic sequence and the molecular and supramolecular structures of six examples

A concise and efficient synthesis of a series of amino‐substituted benzimidazole–pyrimidine hybrids has been developed, starting from the readily available N⁴‐(2‐aminophenyl)‐6‐methoxy‐5‐nitrosopyrimidine‐2,4‐diamine. In each of N⁵‐benzyl‐6‐methoxy‐4‐(2‐phenyl‐1H‐benzo[d]imidazol‐1‐yl)pyrimidine‐2,5‐diamine, C₂₅H₂₂N₆O, (I), 6‐methoxy‐N⁵‐(4‐methoxybenzyl)‐4‐[2‐(4‐methoxyphenyl)‐1H‐benzo[d]imidazol‐1‐yl]pyrimidine‐2,5‐diamine, C₂₇H₂₆N₆O₃, (III), 6‐methoxy‐N⁵‐(4‐nitrobenzyl)‐4‐[2‐(4‐nitrophenyl)‐1H‐benzo[d]imidazol‐1‐yl]pyrimidine‐2,5‐diamine, C₂₅H₂₀N₈O₅, (IV), the molecules are linked into three‐dimensional framework structures, using different combinations of N—H…N, N—H…O, C—H…O, C—H…N and C—H…π hydrogen bonds in each case. Oxidative cleavage of 6‐methoxy‐N⁵‐(4‐methylbenzyl)‐4‐[2‐(4‐methylphenyl)‐1H‐benzo[d]imidazol‐1‐yl]pyrimidine‐2,5‐diamine, (II), with diiodine gave 6‐methoxy‐4‐[2‐(4‐methylphenyl)‐1H‐benzo[d]imidazol‐1‐yl]pyrimidine‐2,5‐diamine, which crystallized as a monohydrate, C₁₉H₁₈N₆O·H₂O, (V), and reaction of (V) with trifluoroacetic acid gave two isomeric products, namely N‐{5‐amino‐6‐methoxy‐6‐[2‐(4‐methylphenyl)‐1H‐benzo[d]imidazol‐1‐yl]pyrimidin‐2‐yl}‐2,2,2‐trifluoroacetamide, which crystallized as an ethyl acetate monosolvate, C₂₁H₁₇F₃N₆O₂·C₄H₈O₂, (VI), and N‐{2‐amino‐6‐methoxy‐4‐[2‐(4‐methylphenyl)‐1H‐benzo[d]imidazol‐1‐yl]pyrimidin‐5‐yl}‐2,2,2‐trifluoroacetamide, which crystallized as a methanol monosolvate, C₂₁H₁₇F₃N₆O₂·CH₄O, (VIIa). For each of (V), (VI) and (VIIa), the supramolecular assembly is two‐dimensional, based on different combinations of O—H…N, N—H…O, N—H…N, C—H…O and C—H…π hydrogen bonds in each case. Comparisons are made with some related structures.     

Six closely related 4,6‐disubstituted 2‐amino‐5‐formylpyrimidines: different ring conformations,polarized electronic structures,and hydrogen‐bonded assembly in zero,one, two and three dimensions

In each of ethyl N‐{2‐amino‐5‐formyl‐6‐[methyl(phenyl)amino]pyrimidin‐4‐yl}glycinate, C₁₆H₁₉N₅O₃, (I), N‐{2‐amino‐5‐formyl‐6‐[methyl(phenyl)amino]pyrimidin‐4‐yl}glycinamide, C₁₄H₁₆N₆O₂, (II), and ethyl 3‐amino‐N‐{2‐amino‐5‐formyl‐6‐[methyl(phenyl)amino]pyrimidin‐4‐yl}propionate, C₁₇H₂₁N₅O₃, (III), the pyrimidine ring is effectively planar, but in each of methyl N‐{2‐amino‐6‐[benzyl(methyl)amino]‐5‐formylpyrimidin‐4‐yl}glycinate, C₁₆H₁₉N₅O₃, (IV), ethyl 3‐amino‐N‐{2‐amino‐6‐[benzyl(methyl)amino]‐5‐formylpyrimidin‐4‐yl}propionate, C₁₈H₂₃N₅O₃, (V), and ethyl 3‐amino‐N‐[2‐amino‐5‐formyl‐6‐(piperidin‐4‐yl)pyrimidin‐4‐yl]propionate, C₁₅H₂₃N₅O₃, (VI), the pyrimidine ring is folded into a boat conformation. The bond lengths in each of (I)–(VI) provide evidence for significant polarization of the electronic structure. The molecules of (I) are linked by paired N—H...N hydrogen bonds to form isolated dimeric aggregates, and those of (III) are linked by a combination of N—H...N and N—H...O hydrogen bonds into a chain of edge‐fused rings. In the structure of (IV), molecules are linked into sheets by means of two hydrogen bonds, both of N—H...O type, in the structure of (V) by three hydrogen bonds, two of N—H...N type and one of C—H...O type, and in the structure of (VI) by four hydrogen bonds, all of N—H...O type. Molecules of (II) are linked into a three‐dimensional framework structure by a combination of three N—H...O hydrogen bonds and one C—H...O hydrogen bond.     

A Novel and Efficient Synthesis of 3‐[(4,5‐Dihydro‐1H‐pyrrol‐3‐yl)carbonyl]‐2H‐chromen‐2‐ones (=3‐[(4,5‐Dihydro‐1H‐pyrrol‐3‐yl)carbonyl]‐2H‐1‐benzopyran‐2‐ones)

An efficient one‐pot synthesis of 3‐[(4,5‐dihydro‐1H‐pyrrol‐3‐yl)carbonyl]‐2H‐chromen‐2‐one (=3‐[(4,5‐dihydro‐1H‐pyrrol‐3yl)carbonyl]‐2H‐1‐benzopyran‐2‐one) derivatives 4 by a four‐component reaction of a salicylaldehyde 1 , 4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one, a benzylamine 2 , and a diaroylacetylene (=1,4‐diarylbut‐2‐yne‐1,4‐dione) 3 in EtOH is reported. This new protocol has the advantages of high yields (Table), and convenient operation. The structures of these coumarin (=2H‐1‐benzopyran‐2‐one) derivatives, which are important compounds in organic chemistry, were confirmed spectroscopically (IR, ¹H‐ and ¹³C‐NMR, and EI‐MS) and by elemental analyses. A plausible mechanism for this reaction is proposed (Scheme 2).     

Synthesis and Characterization of β‐Diketiminate Aluminum Compounds and Their Use in the Ring‐Opening Polymerization of ε‐Caprolactone

Four aluminum alkyl compounds, [CH{(CH₃)CN‐2,4,6‐MeC₆H₂}₂AlMe₂] ( 1 ), [CH{(CH₃)CN‐2,4,6‐MeC₆H₂}₂AlEt₂] ( 2 ), [CH{(CH₃)CN‐2‐iPrC₆H₄}₂AlMe₂] ( 3 ), and [CH{(CH₃)CN‐2‐iPrC₆H₄}₂AlEt₂] ( 4 ), bearing β‐diketiminate ligands [CH{(Me)CN‐2,4,6‐MeC₆H₂}]₂ (L¹H) and [CH{(Me)CN‐2‐ⁱPrC₆H₄}]₂ (L²H) were obtained from the reactions of trimethylaluminum, triethylaluminum with the corresponding β‐diketiminate, respectively. All compounds were characterized by ¹H NMR and ¹³C NMR spectroscopy, single‐crystal X‐ray structural analysis, and elemental analysis. Compounds 1 – 4 were found to catalyze the ring‐opening polymerization (ROP) of ε‐caprolactone (ε‐CL) with good activity.     

Highly Efficient Direct Synthesis of Scaffold 9a,10,12,12a‐Tetrahydrobenzo[b]cyclopenta[f]pyrrolo[1,2‐d][1,4]diazepinone by Using Active Phoshomolybdic Acid

Domino coupling of furan‐2‐yl (phenyl) methanol and 2‐(1H‐pyrrol‐1‐yl) aniline has been achieved in the presence of 10 mol% phosphomolybdic acid in CH₃CN under reflux to afford the corresponding biologically active 10‐aryl‐9a,10,12,12a‐tetrahydrobenzo[b]cyclopenta[f]pyrrolo[1,2‐d][1,4]diazepin‐11(9H)‐ones in good yields. Broad substrate scope, short reaction times, environmentally benign, and operational simplicity makes this method more attractive.     

Synthesis,characterization and cytotoxic activity of 5,10,15,20‐tetrakis[4‐(triorganostannyloxy)phenyl]porphyrins

5,10,15,20‐Tetrakis[4‐(triorganostannyloxy)phenyl]porphyrins, (R₃SnO)₄TPP [2, R = Cy (a), Ph (b), PhC(CH₃)₂CH₂ (c)], have been synthesized by the condensation of 4‐(triorganostannyloxy)benzaldehyde, 4‐(R₃SnO)C₆H₄CHO (1), with pyrrole in the presence of BF₃ followed by oxidation by p‐chloranil and characterized by means of elemental analysis, IR, UV–visible and NMR (¹H, ¹³C and ¹¹⁹Sn) spectra. The results of X‐ray single‐crystal diffraction show that 1a and 1b possess a trans‐C₃SnO₂ trigonal bipyramidal geometry with the axial positions occupied by the phenolate oxygen and formyl group oxygen of an adjacent molecule and form a one‐dimensional zigzag chain. In 2a, the macrocyclic core of the porphyrin is coplanar and each tin atom possesses a distorted tetrahedral geometry. These compounds (1 and 2) have potent in vitro cytotoxic activity against two human tumor cell lines – CoLo205 and MCF‐7 – and the activity decreases in the order Ph > Cy > PhC(CH₃)₂CH₂ for the R group bound to tin. Copyright © 2013 John Wiley & Sons, Ltd.     

Luminescent Amphiphilic 2,6‐Bis(1,2,3‐triazol‐4‐yl)pyridine?Platinum(II) Complexes: Synthesis,Characterization, Electrochemical,Photophysical, and Langmuir–Blodgett Film‐Formation Studies

A new series of platinum(II) complexes with tridentate ligands 2,6‐bis(1‐alkyl‐1,2,3‐triazol‐4‐yl)pyridine and 2,6‐bis(1‐aryl‐1,2,3‐triazol‐4‐yl)pyridine (N7R), [Pt(N7R)Cl]X ( 1 – 7 ) and [Pt(N7R)(C?CR′)]X ( 8 – 17 ; R=n‐C₄H₉, n‐C₈H₁₇, n‐C₁₂H₂₅, n‐C₁₄H₂₉, n‐C₁₈H₃₇, C₆H₅, and CH₂‐C₆H₅; R′=C₆H₅, C₆H₄‐CH₃‐p_, C₆H₄‐CF₃‐p, C₆H₄‐N(CH₃)₂‐p, and cholesteryl 2‐propyn‐1‐yl carbonate; X=OTf^?, PF₆^?, and Cl^?), has been synthesized and characterized. Their electrochemical and photophysical properties have also been studied. Two amphiphilic platinum(II)? 2,6‐bis(1‐dodecyl‐1,2,3‐triazol‐4‐yl)pyridine complexes ( 3‐Cl and 8 ) were found to form stable and reproducible Langmuir–Blodgett (LB) films at the air/water interface. These LB films were characterized by the study of their surface‐pressure–molecular‐area (π–A) isotherms, XRD, and IR and polarized‐IR spectroscopy.     

Synthesis of N,N′,X‐tridentate 2‐iminomethylpyrrole‐coordinated palladium(II) complexes via N─H bond activation of pyrrole moiety

The reaction of [Pd(CH₃CN)₂Cl₂] with N ‐functional group‐substituted 2‐iminomethylpyrrole‐based ligands, namely N ¹‐((1H‐pyrrol‐2‐yl)methylene)‐N ³,N ³‐dimethylpropane‐1,3‐diamine (L_A), N ¹‐((1H‐pyrrol‐2‐yl)methylene)‐N ³‐methyl‐N ³‐phenylpropane‐1,3‐diamine (L_B), N ‐((1H‐pyrrol‐2‐yl)methylene)‐3‐(methylthio)propan‐1‐amine (L_C) and N ‐((1H‐pyrrol‐2‐yl)methylene)‐3‐methoxypropan‐1‐amine (L_D), resulted in [L_n PdCl] (L_n  = L_A–L_D) complexes in high yield via N─H bond activation of pyrrole moiety without use of base. [L_n PdCl] existed as monomeric four‐coordinated complexes with slightly distorted square planar geometries around the palladium metal center. The ligands show N ,N ′,X ‐tridentate binding mode to the palladium metal center to give two fused ring metallacycles. [L_BPdCl] gave the highest activity (3.29 × 10⁵ g PMMA (mol Pd)⁻¹ h⁻¹) for a methyl methacrylate (MMA) polymerization in the presence of modified methylaluminoxane at 60 °C compared to the other Pd(II) analogues, and resulted in PMMA with higher molecular weight (M _w = 7.16 × 10⁵ g mol⁻¹) and narrower polydispersity index. Syndiotactic‐enriched PMMA resulted in all cases.     

Synthesis and Characterization of New Thebaine Derivatives as Potential Opioid Agonists and Antagonists: 2‐[N‐(1H‐Tetrazol‐5‐yl)‐6,14‐endo‐etheno‐6,7,8,14‐tetrahydrothebaine‐7α‐yl]‐5‐phenyl‐1,3,4‐oxadiazoles

In this study, we report the synthesis a series of novel 2‐[N‐(1H‐tetrazol‐5‐yl)‐6,14‐endo‐etheno‐6,7,8,14‐tetrahydrothebaine‐7α‐yl]‐5‐phenyl‐1,3,4‐oxadiazole derivatives ( 7a – e ) which have potential opioid antagonist and agonist. The substitution reaction of 6,14‐endo‐ethenotetrahydrothebaine‐7α‐carbohydrazide with corresponding benzoyl chlorides gave diacylhydrazine compounds 4a – e in good yields. The treatment of compounds 4a – e with POCl₃ caused the conversion of side‐chain of compounds 5a – e into 1,3,4‐oxadiazole ring at C(7) position; thus, compounds 5a – e were obtained. Subsequently, cyanamides ( 6a – e ) were prepared from compounds 5a – e and then compounds 7a – e were synthesized by the azidation of 6a – e with NaN₃. The structures of the compounds were established on the basis of their IR, ¹H NMR, ¹³C APT, 2D‐NMR (COSY, NOESY, HMQC, HMBC) and high‐resolution mass spectral data.     

Syntheses and structures of three macrocyclic supramolecular complexes and one ZnII‐containing coordination polymer generated from a semi‐rigid multidentate N‐containing ligand

Semirigid organic ligands can adopt different conformations to construct coordination polymers with more diverse structures when compared to those constructed from rigid ligands. A new asymmetric semirigid organic ligand, 4‐{2‐[(pyridin‐3‐yl)methyl]‐2H‐tetrazol‐5‐yl}pyridine ( L ), has been prepared and used to synthesize three bimetallic macrocyclic complexes and one coordination polymer, namely, bis(μ‐4‐{2‐[(pyridin‐3‐yl)methyl]‐2H‐tetrazol‐5‐yl}pyridine)bis[dichloridozinc(II)] dichloromethane disolvate, [Zn₂Cl₄(C₁₂H₁₀N₆)₂]·2CH₂Cl₂, ( I ), the analogous chloroform monosolvate, [Zn₂Cl₄(C₁₂H₁₀N₆)₂]·CHCl₃, ( II ), bis(μ‐4‐{2‐[(pyridin‐3‐yl)methyl]‐2H‐tetrazol‐5‐yl}pyridine)bis[diiodidozinc(II)] dichloromethane disolvate, [Zn₂I₄(C₁₂H₁₀N₆)₂]·2CH₂Cl₂, ( III ), and catena‐poly[[[diiodidozinc(II)]‐μ‐4‐{2‐[(pyridin‐3‐yl)methyl]‐2H‐tetrazol‐5‐yl}pyridine] chloroform monosolvate], {[ZnI₂(C₁₂H₁₀N₆)]·CHCl₃}_n, ( IV ), by solution reaction with ZnX₂ (X = Cl and I) in a CH₂Cl₂/CH₃OH or CHCl₃/CH₃OH mixed solvent system at room temperature. Complex ( I ) is isomorphic with complex ( III ) and has a bimetallic ring possessing similar coordination environments for both of the Zn^II cations. Although complex ( II ) also contains a bimetallic ring, the two Zn^II cations have different coordination environments. Under the influence of the I^? anion and guest CHCl₃ molecule, complex ( IV ) displays a significantly different structure with respect to complexes ( I )–( III ). C—H…Cl and C—H…N hydrogen bonds, and π–π stacking or C—Cl…π interactions exist in complexes ( I )–( IV ), and these weak interactions play an important role in the three‐dimensional structures of ( I )–( IV ) in the solid state. In addition, the fluorescence properties of L and complexes ( I )–( IV ) were investigated.     

Structural comparison of group 7 tricarbonyl complexes of 2‐{[2‐(1H‐imidazol‐4‐yl)ethyl]iminomethyl}‐5‐methylphenolate

Two tricarbonyl complexes of rhenium(I) and manganese(I) coordinated by the ligand 2‐{[2‐(1H‐imidazol‐4‐yl)ethyl]iminomethyl}‐5‐methylphenolate are reported, viz. fac‐tricarbonyl(2‐{[2‐(1H‐imidazol‐4‐yl‐κN³)ethyl]iminomethyl‐κN}‐5‐methylphenolato‐κO)rhenium(I) methanol monosolvate, [Re(C₁₆H₁₄N₃O₄)(CO)₃]·CH₃OH, (I), and fac‐tricarbonyl(2‐{[2‐(1H‐imidazol‐4‐yl‐κN³)ethyl]iminomethyl‐κN}‐5‐methylphenolato‐κO)manganese(I), fac‐[Mn(C₁₆H₁₄N₃O₄)(CO)₃], (II), display facial coordination in a distorted octahedral environment. The crystal structure of (I) is stabilized by O—H...O, N—H...O and C—H...O hydrogen‐bond interactions, while that of (II) is stabilized by N—H...O hydrogen‐bond interactions only. These interactions result in two‐dimensional networks and π–π stacking for both structures.     

Synthesis of novel isoindolone‐based medium‐sized macromolecules and triazole containing heterocyclic compounds

A series of novel isoindolone‐based macromolecules of medium‐sized heterocyclic rings, such as 7,8‐dihydro‐6H‐benzo[4,5][1,6,3]dioxazonino[2,3‐a]isoindol‐14(9aH)‐one derivatives ( 5a‐l ), were synthesized and its frame work incorporating with a triazole moiety on phenol, ie, 2‐(4‐((1‐(2‐methoxyphenyl)‐1H‐1,2,3‐triazol‐4‐yl)methoxy)phenyl)isoindoline‐1,3‐dione ( 9a‐f ) and also a triazole moiety on carboxylic acid, ie, (1‐(2‐methoxyphenyl)‐1H‐1,2,3‐triazol‐4‐yl)methyl 4‐(1,3‐dioxoisoindolin‐2‐yl)benzoate derivatives ( 13a‐e ) with various substitutions on aryl ring system have synthesized. All the synthesized compounds were characterized and confirmed with IR, ¹H NMR_, ¹³C NMR, and ESI mass spectral analysis.     

Water Soluble Gold(I)‐diacetyl‐1,3,5‐triaza‐7‐phosphaadamantane‐arylazoimidazole Complexes: Synthesis and Spectroscopic Study

Reaction of [Au(DAPTA)(Cl)] with RaaiR’ in CH2Cl2 medium following ligand addition leads to [Au(DAPTA)(RaaiR’)](Cl) [DAPTA＝diacetyl-1,3,5-triaza-7-phosphaadamantane, RaaiR’＝p-R-C6H4-N＝N- C3H2-NN-1-R’, (1—3), abbreviated as N,N’-chelator, where N(imidazole) and N(azo) represent N and N’, respectively; R＝H (a), Me (b), Cl (c) and R’＝Me (1), CH2CH3 (2), CH2Ph (3)]. The 1H NMR spectral measurements in D2O suggest methylene, CH2, in RaaiEt gives a complex AB type multiplet while in RaaiCH2Ph it shows AB type quartets. 13C NMR spectrum in D2O suggest the molecular skeleton. The 1H-1H COSY spectrum in D2O as well as contour peaks in the 1H-13C HMQC spectrum in D2O assign the solution structure.     

Green Synthesis of 1‐(1,2,4‐Triazol‐4‐yl)spiro[azetidine‐2,3′‐(3H)indole]‐2′,4′(1′H)‐diones as Potential Insecticidal Agents

One pot green synthesis of 1‐(1,2,4‐triazol‐4‐yl)spiro[azetidine‐2,3′‐(3H)‐indole]‐2′,4′(1′H)‐diones was carried out by the reaction of indole‐2,3‐diones,4‐amino‐4H‐1,2,4‐triazole and acetyl chloride/chloroacetyl chloride in ionic liquid [bmim]PF₆ with/without using a catalyst. It was also prepared by conventional method via Schiff's bases, 3‐[4H‐1,2,4‐triazol‐4‐yl]imino‐indol‐2‐one. Further, the corresponding phenoxy derivatives were obtained by the reaction of chloro group attached to azetidine ring with phenols. The synthesized compounds were characterized by analytical and spectral (IR, ¹H NMR, ¹³C NMR, and FAB mass) data. Evaluation for insecticidal activity against Periplaneta americana exhibited promising results.