Shock‐tube spectroscopic water measurements and detailed kinetics modeling of 1‐pentene and 3‐methyl‐1‐butene

To understand the effects of the chemical structure of two C₅ alkene isomers on their combustion properties, and to highlight the major chemical reactions occurring during their high‐temperature oxidation, water time histories were measured behind reflected shock waves for the oxidation of 1‐pentene (C₅H₁₀‐1) and 3‐methyl‐1‐butene (3M1B) in 99.5% Ar. The experiments were carried out at three different equivalence ratios (φ = 0.5, 1.0, and 2.0) at pressures and temperatures ranging from 1.29 to 1.47 atm and 1 331 to 1 877 K, respectively. The H₂O quantification extends the database for 1‐pentene and provides new insights for 3M1B. These unique results were used to validate and to develop a new detailed kinetics model. Numerical predictions are presented, and the new model was able to capture the results with suitable accuracy, with 3M1B being notably more reactive than C₅H₁₀‐1. Sensitivity and rate‐of‐production analyses were performed to help explain the results. Under the present conditions, the reactivity is rapidly initiated by molecular dissociation of a fraction of the pentene isomers. The initiation phase then induces H‐atom abstraction by active radicals (H, OH, O, HO₂, and CH₃) to first produce alkenyl C₅H₉ radicals (or an alkyl radical and an alkenyl radical by breaking a C─C bond) and subsequent, smaller fragments. The difference in terms of reactivity between the isomers is essentially due to the fact that 3M1B has one particularly weak tertiary allylic C─H bond, which allows for fast H‐atom abstraction compared with 1‐pentene.     

Probing long‐range spin–spin coupling constants in 2‐halo‐substituted cyclohexanones and cyclohexanethiones: The role of solvent and stereoelectronic effects

Earlier studies with 2‐bromocyclohexanone demonstrated a measurable long‐range coupling constant (⁴J_H2,H6) for the equatorial conformer, although ⁴J_H2,H4 and ⁴J_H4,H6 were not observed; as a consequence, it is inferred that the carbonyl group plays an important role particularly due to hyperconjugative interactions σ_C2H2→π*_C═O and σ_C6H6→π*_C═O. In the present study, NBO analysis and coupling constant calculations were performed to cyclohexanone and cyclohexanethione alpha substituted with F, Cl, and Br, aiming to evaluate the halogen effect and acceptor character of the π* orbital on the long‐range coupling pathway. The σ_C2H2→π*_C1═Y and σ_C6H6→π*_C1═Y (Y═O and S) hyperconjugative interactions for the equatorial conformer indeed contribute for the ⁴J_H2,H6 transmission mechanism_. Surprisingly, the ⁴J_H2,H6 value is higher for the carbonyl compounds, although the interactions σ_C2H2→π*_C═Y and σ_C6H6→π*_C═Y are more efficient for the thiocarbonyl compounds. Accordingly, the Fermi contact (FC) contribution for the thiocarbonyl compounds decays deeper than in ketones, thus reducing more the ⁴J_H2,H6 values. Moreover, both π_C═S→σ*_C─X and π_C═S→σ*_C─H interactions seem to be stronger in thiocarbonyl than in carbonylic compounds. The implicit solvent effect (DMSO and water) on the coupling constant values was negligible when compared with the gas phase. On the other hand, an explicit solvent effect was found and ⁴J_H2,H6 for the thiocarbonyl compounds appeared to be more sensitive than for the cyclohexanones.     

The Evolution Aspect in the Crystallization Process of [5,5′‐(HCF2CF2CH2OCH2)2‐2,2′‐bpy]MX2 (M = Pt,Pd; X = I,Br): Role of the Intramolecular CF2─H…X(─M) Hydrogen Bonds

The general species (2,2′‐bpy)MX₂ (M = Pd, Pt; X = Br, I) in a crystallization process results in an isomorphous convergence in P2₁/c. Yet, with polyfluorinated side chains, the general [5,5′‐(HCF₂CF₂CH₂OCH₂)₂‐2,2′‐bpy]MX₂ species proceeds to crystallize the isomorphous structures of 5 (M = Pt; X = I) and 6 (M = Pd; X = I) in P2₁/c only; structure 7 (M = Pt; X = Br) crystallizes in P2₁/c but is not isomorphous with 5 and 6 , and structure 8 (M = Pd; X = Br) forms differently in P–1. The causes making the system nonlinear are (1) the intramolecular CF₂─H^…X(─M) hydrogen bonds found in 5–7 but not in 8, and (2) in response to the transition from I to Br, bifurcated [C─H^…]₂ F ─C hydrogen bonds that are formed in 5 and 6 and bifurcated C─ H [^…F─C]₂ hydrogen bonds in 7 . Additionally, the intramolecular CF₂─H^…X(─M) hydrogen bonding from compounds 5–7 could be affirmed by the IR studies.     

Structural studies and cytotoxic activity of a new dinuclear coordination compound of palladium(II)–2,2′:6′,2″‐terpyridine with rigid dianionic 1,2,4‐triazole‐3‐sulfonate linker

A new dinuclear coordination compound of palladium(II), [Pd₂(terpy)₂(μ‐tas‐N¹,N⁴)]SO₄?11H₂O ( 1 ), was synthesized by tethering a doubly deprotonated 1,2,4‐triazole‐3‐sulfonate (tas) linker generated in situ via oxidation of 1,2,4‐triazole‐3‐thione (tat) under the synthetic conditions. X‐ray diffraction analysis reveals that tat molecules adopt the thione form in the solid state, and are combined in infinite chains by symmetrically related classical intermolecular hydrogen bonds N1─H1???S1, N3─H3???N2 to give rise to R₂²(7) pattern in one‐dimensional chains along the b‐axis propagating along the a‐axis. Further short contacts through lone pairs of N2???S1 on the rings between the adjacent chains along the a‐axis lead to a two‐dimensional network structure. Compound 1 was characterized using infrared, ¹H NMR and UV–visible spectroscopies, electrospray ionization mass spectrometry and X‐ray crystallography. The crystal structure determination of 1 reveals that the Pd(II) ions are coordinated with four nitrogen atoms: three from terpy and one from tas acting as an end‐to‐end (μ‐1,4) bridging ligand. The Pd(II) ions in 1 adopt a distorted square planar geometry. The anti‐growth effect of 1 was tested on colorectal cancer (HCT‐15), non‐small‐cell lung cancer (A549), prostate cancer (PC‐3) and cervical cancer (HeLa) cell lines using sulforhodamine B viability assay. The cytotoxic effect was further confirmed using adenosine triphosphate viability assay. Compound 1 shows a promising cytotoxic activity in the diverse cancer cell models in vitro (p <0.0001).     

Three different fluoro‐ or chloro‐substituted 1′‐deoxy‐1′‐phenyl‐β‐D‐ribofuranoses

Crystal structures are reported for three fluoro‐ or chloro‐substituted 1′‐deoxy‐1′‐phenyl‐β‐D‐ribofuranoses, namely 1′‐deoxy‐1′‐(2,4,5‐trifluorophenyl)‐β‐D‐ribofuranose, C₁₁H₁₁F₃O₄, (I), 1′‐deoxy‐1′‐(2,4,6‐trifluorophenyl)‐β‐D‐ribofuranose, C₁₁H₁₁F₃O₄, (II), and 1′‐(4‐chlorophenyl)‐1′‐deoxy‐β‐D‐ribofuranose, C₁₁H₁₃ClO₄, (III). The five‐membered furanose ring of the three compounds has a conformation between a C2′‐endo,C3′‐exo twist and a C2′‐endo envelope. The ribofuranose groups of (I) and (III) are connected by intermolecular O—H...O hydrogen bonds to six symmetry‐related molecules to form double layers, while the ribofuranose group of (II) is connected by O—H...O hydrogen bonds to four symmetry‐related molecules to form single layers. The O...O contact distance of the O—H...O hydrogen bonds ranges from 2.7172 (15) to 2.8895 (19) Å. Neighbouring double layers of (I) are connected by a very weak intermolecular C—F...π contact. The layers of (II) are connected by one C—H...O and two C—H...F contacts, while the double layers of (III) are connected by a C—H...Cl contact. The conformations of the molecules are compared with those of seven related molecules. The orientation of the benzene ring is coplanar with the H—C1′ bond or bisecting the H—C1′—C2′ angle, or intermediate between these positions. The orientation of the benzene ring is independent of the substitution pattern of the ring and depends mainly on crystal‐packing effects.     

A series of substituted (2E)‐3‐(2‐fluoro‐4‐phenoxyphenyl)‐1‐phenylprop‐2‐en‐1‐ones

In the molecular structures of a series of substituted chalcones, namely (2E)‐3‐(2‐fluoro‐4‐phenoxyphenyl)‐1‐phenylprop‐2‐en‐1‐one, C₂₁H₁₅FO₂, (I), (2E)‐3‐(2‐fluoro‐4‐phenoxyphenyl)‐1‐(4‐fluorophenyl)prop‐2‐en‐1‐one, C₂₁H₁₄F₂O₂, (II), (2E)‐1‐(4‐chlorophenyl)‐3‐(2‐fluoro‐4‐phenoxyphenyl)prop‐2‐en‐1‐one, C₂₁H₁₄ClFO₂, (III), (2E)‐3‐(2‐fluoro‐4‐phenoxyphenyl)‐1‐(4‐methylphenyl)prop‐2‐en‐1‐one, C₂₂H₁₇FO₂, (IV), and (2E)‐3‐(2‐fluoro‐4‐phenoxyphenyl)‐1‐(4‐methoxyphenyl)prop‐2‐en‐1‐one, C₂₂H₁₇FO₃, (V), the configuration of the keto group with respect to the olefinic double bond is s‐cis. The molecules pack utilizing weak C—H...O and C—H...π intermolecular contacts. Identical packing motifs involving C—H...O interactions, forming both chains and dimers, along with C—H...π dimers and π–π aromatic interactions are observed in the fluoro, chloro and methyl derivatives.     

Direct oxidative esterification of toluene with 1,3‐dicarbonyl compounds catalysed by copper complex supported on magnetic nanoparticles

Toluene oxidation is one of the substantial industrial technologies since oxidized products are industrially very important intermediates. A Fe₃O₄@cysteine@Cu‐catalysed reaction that uses tert ‐butyl hydroperoxide as oxidant to produce esters from toluene and β‐diketones or β‐keto esters, enolate precursors, has been developed. Oxidative esterification of toluene with 1,3‐dicarbonyl derivatives led to C─O bond formation and direct C─H functionalization.     

Three polymorphs of 3‐(3‐phenyl‐1H‐1,2,4‐triazol‐5‐yl)‐2H‐1‐benzopyran‐2‐one formed from different solvents

The polymorphic study of 3‐(3‐phenyl‐1H‐1,2,4‐triazol‐5‐yl)‐2H‐1‐benzopyran‐2‐one, C₁₇H₁₁N₃O₂, was performed due to its potential biological activity and revealed three polymorphic modifications in the triclinic space group P, the monoclinic space group P2₁ and the orthorhombic space group Pbca. These polymorphs have a one‐column layered type of crystal organization. The strongest interactions between the molecules of the studied structures is stacking between π‐systems, while N—H…N and C—H…O hydrogen bonds link stacked columns forming layers as a secondary basic structural motif. C—H…π hydrogen bonds were observed between neighbouring layers and their role is the least significant in the formation of the crystal structure. Packing differences between the polymorphic modifications are minor and can be identified only using an analysis based on a comparison of the pairwise interaction energies.     

Three sterically hindered 6‐amino‐5‐cyano‐2‐methyl‐4‐(1‐naphthyl)‐4H‐pyran‐3‐carboxylate derivatives

In the title compounds, 2‐methoxyethyl 6‐amino‐5‐cyano‐2‐methyl‐4‐(1‐naphthyl)‐4H‐pyran‐3‐carboxylate, C₂₁H₂₀N₂O₄, (II), isopropyl 6‐amino‐5‐cyano‐2‐methyl‐4‐(1‐naphthyl)‐4H‐pyran‐3‐carboxylate, C₂₁H₂₀N₂O₃, (III), and ethyl 6‐amino‐5‐cyano‐2‐methyl‐4‐(1‐naphthyl)‐4H‐pyran‐3‐carboxylate, C₂₀H₁₈N₂O₃, (IV), the heterocyclic pyran ring adopts a flattened boat conformation. In (II) and (III), the carbonyl group and a double bond of the heterocyclic ring are mutually anti, but in (IV) they are mutually syn. The ester O atoms in (II) and (III) and the carbonyl O atom in (IV) participate in intramolecular C—H...O contacts to form six‐membered rings. The dihedral angles between the naphthalene substituent and the closest four atoms of the heterocyclic ring are 73.3 (1), 71.0 (1) and 74.3 (1)° for (II)–(IV), respectively. In all three structures, only one H atom of the NH₂ group takes part in N—H...O [in (II) and (III)] or N—H...N [in (IV)] intermolecular hydrogen bonds, and chains [in (II) and (III)] or dimers [in (IV)] are formed. In (II), weak intermolecular C—H...O and C—H...N hydrogen bonds, and in (III) intermolecular C—H...O hydrogen bonds link the chains into ladders along the a axis.     

A comparative study of two polymorphs of bis(1‐hydroxy‐2‐methylpropan‐2‐aminium) carbonate

Alkanolamines have been known for their high CO₂ absorption for over 60 years and are used widely in the natural gas industry for reversible CO₂ capture. In an attempt to crystallize a salt of (RS)‐2‐(3‐benzoylphenyl)propionic acid with 2‐amino‐2‐methylpropan‐1‐ol, we obtained instead a polymorph (denoted polymorph II) of bis(1‐hydroxy‐2‐methylpropan‐2‐aminium) carbonate, 2C₄H₁₂NO⁺·CO₃²⁻, (I), suggesting that the amine group of the former compound captured CO₂ from the atmosphere forming the aminium carbonate salt. This new polymorph was characterized by single‐crystal X‐ray diffraction analysis at low temperature (100 K). The salt crystallizes in the monoclinic system (space group C2/c, Z = 4), while a previously reported form of the same salt (denoted polymorph I) crystallizes in the triclinic system (space group P, Z = 2) [Barzagli et al. (2012). ChemSusChem, 5 , 1724–1731]. The asymmetric unit of polymorph II contains one 1‐hydroxy‐2‐methylpropan‐2‐aminium cation and half a carbonate anion, located on a twofold axis, while the asymmetric unit of polymorph I contains two cations and one anion. These polymorphs exhibit similar structural features in their three‐dimensional packing. Indeed, similar layers of an alternating cation–anion–cation neutral structure are observed in their molecular arrangements. Within each layer, carbonate anions and 1‐hydroxy‐2‐methylpropan‐2‐aminium cations form planes bound to each other through N—H…O and O—H…O hydrogen bonds. In both polymorphs, the layers are linked to each other via van der Waals interactions and C—H…O contacts. In polymorph II, a highly directional C—H…O contact (C—H…O = 156°) shows as a hydrogen‐bonding interaction. Periodic theoretical density functional theory (DFT) calculations indicate that both polymorphs present very similar stabilities.     

The diastereoisomers 2‐[(S/R)‐2‐chloro‐3‐quinolyl]‐2‐[(R)‐1‐(4‐methoxyphenyl)ethylamino]acetonitrile at 100 K

In the structures of the two enantiopure diastereoisomers of the title compound, C₂₀H₁₈ClN₃O, which crystallize in different space groups, the molecules are very similar as far as bond distances and angles are concerned, but more substantial differences are observed in some torsion angles. The crystal structures of both molecules can be described as zigzag layers along the c axis. The packing is stabilized by hydrogen‐bond interactions of N—H...O, C—H...Cl and C—H...π types for 2‐[(R)‐2‐chloro‐3‐quinolyl]‐2‐[(R)‐1‐(4‐methoxyphenyl)ethylamino]acetonitrile, and of N—H...N, C—H...O and C—H...π types for 2‐[(S)‐2‐chloro‐3‐quinolyl]‐2‐[(R)‐1‐(4‐methoxyphenyl)ethylamino]acetonitrile, resulting in the formation of two‐ and three‐dimensional networks.     

Exo conformers of N‐(pyridin‐2‐yl)‐ and N‐(pyridin‐3‐yl)norbornene‐5,6‐dicarboximide crystals

Two isomeric pyridine‐substituted norbornenedicarboximide derivatives, namely N‐(pyridin‐2‐yl)‐exo‐norbornene‐5,6‐dicarboximide, (I), and N‐(pyridin‐3‐yl)‐exo‐norbornene‐5,6‐dicarboximide, (II), both C₁₄H₁₂N₂O₄, have been crystallized and their structures unequivocally determined by single‐crystal X‐ray diffraction. The molecules consist of norbornene moieties fused to a dicarboximide ring substituted at the N atom by either pyridin‐2‐yl or pyridin‐3‐yl in an anti configuration with respect to the double bond, thus affording exo isomers. In both compounds, the asymmetric unit consists of two independent molecules (Z′ = 2). In compound (I), the pyridine rings of the two independent molecules adopt different conformations, i.e. syn and anti, with respect to the methylene bridge. The intermolecular contacts of (I) are dominated by C—H...O interactions. In contrast, in compound (II), the pyridine rings of both molecules have an anti conformation and the two independent molecules are linked by carbonyl–carbonyl interactions, as well as by C—H...O and C—H...N contacts.     

Methyl 2‐benzamido‐4‐(3,4‐dimethoxyphenyl)‐5‐methylbenzoate and N‐{5‐benzoyl‐2‐[(Z)‐2‐methoxyethenyl]‐4‐methylphenyl}benzamide

Methyl 2‐benzamido‐4‐(3,4‐dimethoxyphenyl)‐5‐methylbenzoate, C₂₄H₂₃NO₅, (Ia), and N‐{5‐benzoyl‐2‐[(Z)‐2‐methoxyethenyl]‐4‐methylphenyl}benzamide, C₂₄H₂₁NO₃, (IIa), were formed via a Diels–Alder reaction of appropriately substituted 2H‐pyran‐2‐ones and methyl propiolate or (Z)‐1‐methoxybut‐1‐en‐3‐yne, respectively. Each of these cycloadditions might yield two different regioisomers, but just one was obtained in each case. In (Ia), an intramolecular N—H...O hydrogen bond closes a six‐membered ring. A chain is formed due to aromatic π–π interactions, and a three‐dimensional framework structure is formed by a combination of C—H...O and C—H...π(arene) hydrogen bonds. Compound (IIa) was formed not only regioselectively but also chemoselectively, with just the triple bond reacting and the double bond remaining unchanged. Compound (IIa) crystallizes as N—H...O hydrogen‐bonded dimers stabilized by aromatic π–π interactions. Dimers of (IIa) are connected into a chain by weak C—H...π(arene) interactions.     

The 7‐bromo derivative of 2‐amino‐2′‐deoxytubercidin fluorinated at the sugar moiety

The title compound, 2,4‐diamino‐5‐bromo‐7‐(2‐deoxy‐2‐fluoro‐β‐d ‐arabinofuranosyl)‐7H‐pyrrolo[2,3‐d]pyrimidine, C₁₁H₁₃BrFN₅O₃, shows two conformations of the exocyclic C4′—C5′ bond, with the torsion angle γ (O5′—C5′—C4′—C3′) being 170.1 (3)° for conformer 1 (occupancy 0.69) and 60.7 (7)° for conformer 2 (occupancy 0.31). The N‐glycosylic bond exhibits an anti conformation, with χ = −114.8 (4)°. The sugar pucker is N‐type (C3′‐endo; ³T₄), with P = 23.3 (4)° and τ_m = 36.5 (2)°. The compound forms a three‐dimensional network that is stabilized by several intermolecular hydrogen bonds (N—H...O, O—H...N and N—H...Br).     

One‐step synthesis of 6‐acetamido‐3‐(N‐(2‐(dimethylamino) ethyl) sulfamoyl) naphthalene‐1‐yl 7‐acetamido‐4‐hydroxynaphthalene‐2‐sulfonate and its characterization with 1D and 2D NMR techniques

A one‐step method was reported for the synthesis of 6‐acetamido‐3‐(N‐(2‐(dimethylamino) ethyl) sulfamoyl) naphthalene‐1‐yl 7‐acetamido‐4‐hydroxynaphthalene‐2‐sulfonate by treating 7‐acetamido‐4‐hydroxy‐2‐naphthalenesulfonyl chloride with equal moles of N, N‐dimethylethylenediamine in acetonitrile in the presence of K₂CO₃. The chemical structure of the obtained compounds was characterized by MS, FTIR, ¹H NMR, ¹³C NMR, gCOSY, TOCSY, gHSQC, and gHMBC. The chemical shift differences of ¹H and ¹³C being δ 0.04 and 0.2, respectively, were unambiguously differentiated. Copyright © 2013 John Wiley & Sons, Ltd.     

Hydrogen‐bonding patterns in three substituted N‐benzyl‐N‐(3‐tert‐butyl‐1‐phenyl‐1H‐pyrazol‐5‐yl)acetamides

The molecules of N‐(3‐tert‐butyl‐1‐phenyl‐1H‐pyrazol‐5‐yl)‐2‐chloro‐N‐(4‐methoxybenzyl)acetamide, C₂₃H₂₆ClN₃O₂, are linked into a chain of edge‐fused centrosymmetric rings by a combination of one C—H...O hydrogen bond and one C—H...π(arene) hydrogen bond. In N‐(3‐tert‐butyl‐1‐phenyl‐1H‐pyrazol‐5‐yl)‐2‐chloro‐N‐(4‐chlorobenzyl)acetamide, C₂₂H₂₃Cl₂N₃O, a combination of one C—H...O hydrogen bond and two C—H...π(arene) hydrogen bonds, which utilize different aryl rings as the acceptors, link the molecules into sheets. The molecules of S‐[N‐(3‐tert‐butyl‐1‐phenyl‐1H‐pyrazol‐5‐yl)‐N‐(4‐methylbenzyl)carbamoyl]methyl O‐ethyl carbonodithioate, C₂₆H₃₁N₃O₂S₂, are also linked into sheets, now by a combination of two C—H...O hydrogen bonds, both of which utilize the amide O atom as the acceptor, and two C—H...π(arene) hydrogen bonds, which utilize different aryl groups as the acceptors.     

6‐(2‐Hydro­xy­benzoyl)‐5‐(pyrrol‐2‐yl)‐3H‐pyrrolizine

The title compound, 2‐hydroxy­phenyl 5‐(pyrrol‐2‐yl)‐3H‐pyrrolizin‐6‐yl ketone, C₁₈H₁₄N₂O₂, was isolated from the base‐catalyzed 1:2 condensation of 2‐hydroxy­aceto­phenone with pyrrole‐2‐carbaldehyde. The pyrrole N—H and hydroxy­benzoyl O—H groups are hydrogen bonded to the benzoyl O atom. The allyl­ic C=C double bond of the 3H‐pyrrolizine system is located between ring positions 1 and 2, the C atom at position 3 (adjacent to the N atom) being single bonded.     

Hydrogen‐bonded chains of rings in 1‐(4‐chloroanilinomethyl)‐5‐(4‐chlorophenyl)‐1,3,5‐triazinane‐2‐thione and hydrogen‐bonded sheets in 1‐anilinomethyl‐5‐phenyl‐1,3,5‐triazinane‐2‐thione

In 1‐(4‐chloroanilinomethyl)‐5‐(4‐chlorophenyl)‐1,3,5‐triazinane‐2‐thione, C₁₆H₁₆Cl₂N₄S, there are two independent molecules in the asymmetric unit which form inversion dimers via two weak N—H...S hydrogen bonds. The dimers are then linked into C(9)C(14) chains by a C—H...S hydrogen bond and a C—H...Cl contact. In 1‐(anilinomethyl)‐5‐phenyl‐1,3,5‐triazinane‐2‐thione, C₁₆H₁₈N₄S, molecules are linked into complex sheets via a combination of N—H...S and C—H...π hydrogen bonds.     

(Z)‐5‐[(5‐Methyl‐1H‐imidazol‐4‐yl)methylidene]‐2‐sulfanylidene‐1,3‐thiazolidin‐4‐one monohydrate: a three‐dimensional hydrogen‐bonded framework structure

The non‐H atoms in the organic component of the title compound, C₈H₇N₃OS₂·H₂O, are almost coplanar, as the dihedral angle between the two ring planes is only 1.8 (2)°; there is a wide C—C—C angle of 127.8 (3)° at the methine C atom linking the two rings. The molecular components are linked into a three‐dimensional framework structure by two‐centre hydrogen bonds of N—H...O and O—H...N types, together with a three‐centre O—H...(N,S) system. Comparisons are made with some (Z)‐5‐arylmethylidene‐2‐sulfanylidene‐1,3‐thiazolidin‐4‐ones.     

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.