bluuebunny/crossref_metadata_2025_split huggingface dataset:
8,11 a‐methanocycloocta[d,e]quinazolines: Diisophoranes incorporating the pyrimidine ring system
Authors: Kurzer Frederick , Langer Stanley S. 
Published: March 2009

AbstractThe interaction of 1‐chloro(or hydroxy)diisophor‐2(7)‐en‐3‐one 1 or 3 with guanidines or ureas produces good yields of substituted 8,11a‐methanocycloocta[d,e]quinazolines 5‐11, involving a nucleophilic SN1‐substitution at the 1‐bridgehead and dehydrative cyclisation at the 3‐keto‐group of the tricyclic reactants 1, 3. The structure assigned to members of this novel heterocyclic bridged ring‐system is based on both chemical and carbon nmr spectral evidence. The synthesis provides further variants of the incorporation of a fused heterocyclic ring into the tricyclo[7.3.1.02,7]tridecane carbon skeleton. A related condensed [1,3]oxazine 16 is similarly accessible.
A simple crab‐like cyclization procedure to prepare polyaza‐crowns and cyclams with one or two unsubstituted macroring nitrogen atoms or with a hydroxy group
Authors: Bradshaw Jerald S. , Krakowiak Krzysztof E. , Izatt Reed M. 
Published: March 2009

AbstractA simple and convenient method to prepare polyaza‐crowns and cyclams containing one or two unsubstituted macroring nitrogen atoms or a hydroxy group is described. The process involves the reaction of a bis‐ chloroamide with a bis‐secondary amine followed by reduction of the cyclic diamide. The bis‐chloroamide resembles a crab with two reactive organochloride groups poised and ready to react, hence the term “crab‐like” cyclization. Nine new polyaza‐crowns and cyclams were prepared.
The oxidative‐rearrangement of 1‐amino‐2‐indolinones. A synthesis of 2‐substituted‐3(2H)‐cinnolinones
Authors: Zey R. L. , Richter G. , Randa H. 
Published: March 2009

AbstractSeveral 2‐substituted‐3(2H)‐cinnolinones have been synthesized by a ring expansion of the respective 1‐substituted‐2‐indolinones via an oxidative‐rearrangement with t‐butyl hypochlorite.
Anticancer anilinoacridines. A process synthesis of the disubstituted amsacrine analog CI‐921
Authors: Brennan Sean T. , Colbry Norman L. , Leeds Robert L. , Leja Boguslawa , Priebe Stephen R. , Reily Michael D. , Showalter H. D. Hollis , Uhlendorf Susan E. , Atwell Graham J. , Denny William A. 
Published: March 2009

AbstractAn improved process for the synthesis of bulk quantities of the clinical amsacrine analog CI‐921 is reported. Described also are detailed analytical and spectroscopic data for this agent.
meso‐tetrakis[2.2]paracyclophanylporphyrin: Electronic structure and electrochemical behavior
Authors: Czuchajowski Leszek , Goszczynski Stefan , Wisor Antoni K. , Bennett Janet E. , Malinski Tadeusz 
Published: March 2009

AbstractReplacement of all phenyl groups in meso‐tetraphenylporphyrin, TPP, by [2.2]paracyclophane, PCP, enhances the increase of energy of the HOMO and HOMO‐1 of porphine, P, already noticed for the mono‐[2.2]paracyclophanyl‐substituted TPP, and fills the energy gap by the occupied MOs of the PCP units. The first oxidation half‐wave potential is respectively decreased to 0.52 V. The CNDO/S‐CIS calculations agree with the experimental bathochromic shifts of all bands in the electronic spectra of the considered atropoisomers of the title compound, TPCPP, as compared to TPP. In the excited B states the interactions between the PCP and porphine units are represented mainly by the charge transfer of 0.44 e from PCP to P, according to transition density matrix calculations. While electroreduction of the title compound results in a successive formation of the anion radical and dianion, oxidation represents a four‐step process involving one electron transfer per step, and resulting in the oxidation of two PCP units. Formation of the conductive polymeric film on the electrode seems to be connected with the transient formation of a quinoid system of bonds.
Regioselection in the reaction of 3‐amino‐5‐benzylthio‐1,2,4‐triazole with unsymmetrical 1,3‐diketones
Authors: Kleschick William A. , Bordner Jon 
Published: March 2009

AbstractThe results of a study of the regioselection in the reaction of 3‐amino‐5‐benzylthio‐1,2,4‐triazole with several unsymmetrical 1,3‐diketones are reported. The 1,3‐diketones studied are 1,1,1‐trifluoro‐2,4‐pentanedione, benzoylacetone and 2‐acetylcyclopentanone. Chemical, spectroscopic and X‐ray crystallographic data are presented to support structural assignments of the major reaction products.
Synthesis and biological properties of 3‐methyl‐10‐propargyl‐5,8‐dideazafolic acid
Authors: Jones Terence R. , Betteridge Richard F. , Newell David R. , Jackman Ann L. 
Published: March 2009

AbstractThe synthesis of N3‐methyl‐10‐propargyl‐5,8‐dideazafolic acid (1b) is described. Ring closure of methyl‐5‐methylanthranilate with chloroformamidine hydrochloride gave a high yield of pure 2‐amino‐4‐hydroxy‐6‐methylquinazoline treatment of which with iodomethane/sodium hydroxide provided the corresponding 3‐methylquinazoline (6) which was converted to its 2‐pivaloylamino derivative. This synthetic approach, next involving functionalisation of the 6‐methyl group, was not further pursued because of difficulty encountered in removing the pivaloyl group. Methyl 5‐methylanthranilate was treated with p‐toluenesulfonyl chloride and the product then N‐methylated. The tosyl group was cleaved with hydrogen bromide/phenol and the resulting methylamine ring‐closed with chloroformamidine hydrochloride to provide 2‐amino‐1,4‐dihydro‐1,6‐dimethyl‐4‐oxoquinazoline (11). The 2‐pivaloylamino derivative of 11 was prone to hydrolytic deamination when attempts were made to remove the pivaloyl group and further elaboration of this heterocycle, with the intention of obtaining N1‐methyl‐10‐propargyl‐5,8‐dideazafolic acid was, too, not attempted. Di‐t‐butyl N‐(4‐propargylamino)benzoyl)‐L‐glutamate was therefore prepared and coupled with 2‐amino‐6‐bromomethyl‐4‐hydroxyquinazoline hydrobromide. The resulting antifolate diester was N‐monomethylated. Removal of the t‐butyl groups with trifluoracetic acid afforded the target compound 1b and its structure was proved by degradation to the quinazoline 6. Its IC50 for L1210 thymidylate synthase (TS) was 26 μM; the control value for 10‐propargyl‐5,8‐dideazafolic acid (1a) was 0.02 μM. Thus the substitution of the lactam hydrogen in 1a by a methyl group reduced the TS inhibition by 1300‐fold. Compound 1b was poorly cytotoxic to L1210 cells in culture (ID50 > 100 μM). An unperturbed lactam group in this class of antifolate is important for binding to TS.
The synthesis of 5,8‐difluoronaphtho[2,3‐c]thiophene‐4,9‐dione and its facile conversion to 2‐[2‐(dimethylamino)ethyl]‐ 5‐[2‐(dimethylamino)ethylamino]‐8‐fluoro‐naphtho[2,3‐c] pyrrole‐4,9‐dione
Authors: Krapcho A. Paul , Petry Mary E. 
Published: March 2009

AbstractThe synthesis of 5,8‐difluoronaphtho[2,3‐c]thiophene‐4,9‐dione (2a) has been accomplished. Treatment of 2a with 2,2‐dimethylaminoethylamine leads to 2‐[2‐(dimethylamino)ethyl]‐5‐[2‐(dimethylamino)ethylamino]‐8‐fluoronaphtho[2,3‐c]pyrrole‐4,9‐dione (6).
A convenient synthesis of novel pyridazino[3,4‐b]quinoxaline and pyrazolo[3,4‐b]quinoxaline utilizing 1,3‐dipolar cycloaddition reaction
Authors: Kim Ho Sik , Kurasawa Yoshihisa , Takada Atsushi 
Published: March 2009

AbstractThe reaction of 2,6‐dichloroquinoxaline 4‐oxide 4 with methylhydrazine gave 6‐chloro‐2‐(1‐methylhydrazino)quinoxaline 4‐oxide 5, whose reaction with dimethyl acetylenedicarboxylate or 2‐chloroacrylonitrile resulted in the 1,3‐dipolar cycloaddition reaction to afford 7‐chloro‐3,4‐bismethoxycarbonyl‐1‐methyl‐1,2‐dihydropyridazino[3,4‐b]quinoxaline 6 or 6‐chloro‐3‐hydroxymethylene‐1‐methyl‐2,3‐dihydro‐1H‐pyrazolo[3,4‐b] quinoxaline hydrochloride 7, respectively.
One‐step syntheses of macrocyclic compounds: A short review
Authors: Krakowiak Krzysztof E. , Izatt Reed M. , Bradshaw Jerald S. 
Published: March 2009

AbstractMacrocyclic ligands have been prepared by various one‐step cyclooligomerization processes. This short review covers one‐step cyclization reactions involving the formation of four to twenty or more new covalent bonds. The new macrocycles reviewed include cyclophanes, biscrown ethers, cryptands, macrolides, cage compounds, calixarenes, homocalixarenes, cucubiturils, and supercryptands all prepared by one‐step syntheses.
Sonochemical reformatsky reactions of α‐bromoesters with sym‐(keto)dibenzo‐16‐crown‐5
Authors: Ross Nathan A. , Bartsch Richard A. 
Published: March 2009

AbstractReactions of sym‐(keto)dibenzo‐16‐crown‐5 with ethyl α‐bromoesters, zinc dust and iodine in dioxane and/or tetrahydrofuran under irradiation by high intensity ultrasound (HIU) provide β‐hydroxy lariat ether esters in 79‐91% yields. HIU‐promoted Reformatsky reactions offer several advantages over customary thermal reaction conditions.
Synthesis and coordination properties of highly preorganised polyamine macrocycles
Authors: Bazzicalupi Carla , Bencini Andrea , Bianchi Antonio , Giorgi Claudia , Paoletti Piero , Valtancoli Barbara , Fusi Vieri , Garcia‐Españta Enrique , Llinares Josè M. 
Published: March 2009

AbstractSynthesis and characterisation of the new macrocyclic ligands L1‐L4 are reported. The ligands present one or two pentaamine moieties, each containing two piperazine rings, linked by benzene or anthracene spacers. Interaction of L1 with H+, Cu(II), Zn(II), Hg(II), and Pd(II) and of L3 with H+, and Cu(II) has been studied by potentiometric titrations in 0.15 mol dm−3 NaCl aqueous solution at 298.1 ±0.1 K. The thermodynamic data suggest that in the metal complexes only three nitrogen donor atoms bind each metal ion. As a consequence of the low coordination number, these complexes are promising receptors for different molecules.
Synthesis of 2‐silaoxane via 1,3‐ photocycloaddition
Authors: Bahu Suhail , Fleming Steven A. , Nilsson Brad , Turner Tim 
Published: March 2009

AbstractIrradiation of an aryl group with a silyl tethered alkene yields a tetracyclic 2‐silaoxane with high regiose‐lectivity. The multicyclic structure has been further modified to give an unstable tricyclic diol. Photocycloaddition between cyclopentene and phenylcyclopropane gave a single major cycloadduct without cyclopropyl ring opening, indicating that the putative radical intermediate involved in cycloaddition apparently has a very short lifetime if it exists at all.
Synthesis, alkali metal picrate extraction, and alkali metal cation binding selectivities of some new cage‐annulated polyoxamacrocyclic crown ethers
Authors: Marchand Alan P. , Huang Zilin , Chen Zhibing , Hariprakasha H. K. , Namboothiri I. N. N. , Brodbelt Jennifer S. , Reyzer Michelle L. 
Published: March 2009

AbstractFive new cage‐annulated crown ethers, i.e., 4a, 4b, 6b, 11a, and 11b, have been synthesized and their respective alkali metal picrate extraction profiles along with that of a previously synthesized host molecule, 6a, have been obtained. These results are compared with the corresponding results obtained for electrospray ionization mass spectrometric (ESI‐MS) measurements of relative binding selectivities displayed by the same hosts toward a series of alkali metal chlorides. Among the crown‐5 hosts studied, 6a displays enhanced avidity toward complexation with K+ picrate in liquid‐liquid extraction experiments. Among the three crown‐6 hosts, 4b proved to be the best alkali metal picrate extractant and displayed significant levels of avidity toward complexation with the larger alkali metal cations (i.e., K+, Rb+, and Cs+). The trends in the picrate extraction and the ESI‐MS results obtained herein show several notable similarities and some differences. The similarities generally stem from size‐selective binding properties that are intrinsic to the different cavity sizes of the cage‐annulated macrocycles, whereas the differences reflect the important influence of solvation effects on the binding properties of the macrocycles.
New diazadi(and tri)thia‐21‐crown‐7 ethers containing 8‐hydroxyquinoline side arms
Authors: Song Hua‐Can , Chen Yi‐Wen , Song Ji‐Guo , Savage Paul B. , Xue Guo‐Ping , Chiara Joseph A. , Izatt Reed M. , Bradshaw Jerald S. , Krakowiak Krzysztof E. 
Published: March 2009

AbstractA series of macrocyclic diazadi(and tri)thiacrown ethers containing two 5‐substituent‐8‐hydroxyquinoline side arms have been synthesized from the corresponding macrocyclic diazadi(and tri)thiacrown ethers. The crown ethers were obtained by reduction of the proper macrocyclic di(and tri)thiadiamides by borane‐tetrahydrofuran or by sodium borohydride‐boron trifluoride ethyl etherate‐tetrahydrofuran. The yields for the reduction of diamides by sodium borohydride‐boron trifluoride ethyl etherate‐tetrahydrofuran were higher than those by borane‐tetrahydrofuran. The following four methods were used to prepare macrocycles bearing two 8‐hydroxyquinoline side arms: (1) Mannich reaction with 8‐hydroxyquinoline; (2) Reductive animation with 8‐hydroxyquinoline‐2‐carboxaldehyde using sodium triacetoxyborohydride as the reducing agent; (3) Cyclization of N,N'‐bis(8‐hydroxyquinolin‐2‐ylmethyl)‐1,2‐bis(2‐aminoethoxy)ethane (38) with bis(α‐chloroamide) 5; and (4) A step‐by‐step process wherein macrocyclic trithiadiamide 11 was reduced by lithium aluminum hydride‐tetrahydrofuran to the cyclic monoamide 36, which smoothly reacted with 5‐chloro‐8‐hydroxyquinoline to produce monosubstituted‐macrocyclic monoamide 39.
Novel calix[4]cryptands: “Mappemonde II” and “Mill II”
Authors: Pulpoka Buncha , Kim Jong Sueng , Yang Seung Hwan , Vicens Jacques 
Published: March 2009

AbstractTwo novel calix[4]cryptands were synthesized from 1,3‐alternate calix[4]bis‐azacrown. “Mappemonde II” consists of one 1,3‐calix[4]bis‐azacrown wrapped by a benzo‐crown ether loop. “Mill II” is composed of two 1,3‐calix[4]bis‐azacrowns linked by two benzo‐crown ether strands.
A density functional theoretical study of the influence of cavities and water molecules on tautomerism: The case of pyridones and 1,2,4‐triazoles linked to crown ethers and esters
Authors: Alkorta Ibon , Elguero José 
Published: March 2009

AbstractThe tautomerism of pyridones and 1,2,4‐triazoles related to two crown ethers and two crown esters derived from these heterocycles was studied theoretically. For the four macrocycles, Bradshaw identified a single tautomer by X‐ray crystallography. To rationalize these findings, a series of calculations from simple models to crown derivatives have been carried out. The most interesting case concerns the observation, for the first time, of a 4H‐1,2,4‐triazole tautomer. To explain this result it was necessary to calculate the whole crown ester plus a caged water molecule was necessary.
The effect of twin‐tailed sidearms on sodium cation transport in synthetic hydraphile cation channels
Authors: Shabany Hossein , Pajewski Robert , Abel Ernesto , Mukhopadhyay Anindita , Gokel George W. 
Published: March 2009

AbstractThe preparation of novel tris(macrocycle)s that transport Na+ through phospholipid bilayers is reported. All of the reported structures have the following structural elements: sidechain‐macrocycle‐spacer‐macro‐cycle‐spacer‐macrocycle‐sidechain. The overall extension of the channel system is defined by the lengths of the spacer chains. The flexible sidearms are thought to be aligned with the lipid axis and opposite to the spacer chains. To the extent the spacer chains contribute to organization of the structure and isolation of the cation‐containing pore from the surrounding lipid chains, more hydrophobic chains are expected to enhance cation transport. A comparison of C12H25<N18N>(CH2)12<N18N>(CH2)12<N18N> C12H25, 1, with (C12H25)2N(CH2)2<N18N>(CH2)12<N18N>(CH2)12<N18N>(CH2)2N(C12H25)2, 11, shows that the Na+ transport is, indeed, enhanced.
Crown ether strategy toward chemical activation of biological protein functions
Authors: Tsukube Hiroshi , Yamada Takashi , Shinoda Satoshi 
Published: March 2009

AbstractThe chemical activation of biological proteins is outlined, in which small molecules are used to alter the chemical and physical properties of biological proteins through direct or indirect interactions. Crown ethers have the potential to modulate the protein functions by supramolecular complexations, because they bind alkylammonium and other ionic residues of the proteins as well as ionic components in their systems. Two interesting examples are described in which crown ether derivatives improved the protein functions: (1) enhancement of reactivity and enantioselectivity in lipase‐catalyzed asymmetric reactions; and (2) generation of catalytic activity in the oxidation with cytochrome c. This chemical activation based on crown ether chemistry can be viewed as a complementary method to biological mutation in modifying the biological protein functions.
Synthesis of 7‐acetyloxy‐3,7‐dimethy1‐7,8‐dihydro‐6H‐isochromene‐6,8‐dione and its analogues
Authors: Suzuki Tsuneo , Tanemura Kiyoshi , Okada Chizuko , Arai The Late Kenichi , Awaji Akira , Shimizu Takahachi , Horaguchi Takaaki 
Published: March 2009

Abstract7‐Alkanoyloxy‐3,7‐dimefhyl‐7,8‐dihydro‐6H‐isochromene‐6,8‐diones 12‐15 were synthesized in 69‐16% yields from the reaction of 2,4‐dihydroxy‐3‐methyl‐6‐(2‐oxopropyl)benzaldehyde 11 with p‐toluenesulfonic acid in various carboxylic acids such as acetic acid, propionic acid, butyric acid and heptanoic acid followed by oxidation with lead tetraacetate. On the other hand, (±)‐daldinin A 5 (oleate) was not obtained using oleic acid as a medium. In the cases of heptanoic acid and oleic acid, esters 16 and 17 were produced in 23 and 9% yields, respectively. 6,8‐Dihydroxy‐3,7‐dimethyl‐2‐benzopyrylium p‐toluenesulfonate 31 is considered as the intermediate for the production of 12‐15. Overall yields of isochromenes 12‐15 were 26‐6% starting from 2‐methylresorcinol for seven steps.
Dioxa‐[40]decaphyrin(1.0.1.0.0.1.0.1.0.0): An analogue of turcasarin with a “figure‐eight” structure
Authors: Sessler Jonathan L. , Seidel Daniel , Gebauer Andreas , Lynch Vincent , Abboud Khalil A. 
Published: March 2009

AbstractThe synthesis and characterization of two different furan containing analogues of turcasarin, namely 46,51 ‐dioxa‐2,11,15,20,24,33,37,42‐octapropyl‐turcasarin (7a) and 46,51 ‐dioxa‐2,11,24,33‐tetrapropyl‐15,20,37,42‐tetraethyl‐16,19,38,41‐tetramethyl‐turcasarin (7b) are described. While 7a was found to exhibit a “figure eight” structure in solution and in the solid state, 7b is believed to adopt a different, more symmetric conformation is solution.
New isomeric 2‐ortho‐(meta‐ and para‐) chloro‐(bromo and nitro‐)benzylthio‐6‐aminouracils
Authors: Wyrzykiewicz Elżbieta , Szponar Anna 
Published: March 2009

AbstractTen new ortho, meta and para substituted derivatives of 2‐benzylthio‐6‐aminouracils have been prepared. Electron Impact (EI) induced mass spectral fragmentation of these compounds was investigated. Fragmentation pathways are proposed on the basis of accurate mass and metastable transition measurements. The correlation between the intensities of the M+‐ and the selected fragment ions of these compounds is discussed. The data obtained create the basis for dinstinguishing isomers. The 1H and 13C NMR spectra of these compounds were assigned unambiguously using a combination of heteronuclear (HETCOR) spectra the chemical shifts. The data derived from these spectra can be used to differentiate the isomers.
Synthesis of 1,3,4‐oxa(or thia)diazaheterocycles starting from 2‐(pyrrol‐1'‐y1)phthalimide
Authors: Guesdon Anita , Fogain‐Ninkam Alain , Decroix Bernard , Netchitaïlo Pierre 
Published: March 2009

Abstract1‐(1,3‐Dioxo‐1,3‐dihydro‐2H‐isoindol‐2‐yl)‐1H‐pyrrol‐2 carbaldehyde 4 was synthesized by Vilsmeier‐Haack reaction from 2‐(pyrrol‐1‐yl) phthalimide. Reduction of 4 by sodium borohydride, or action of Grignard reagents on 4 led to the corresponding alcohols 5 which were cyclized to pyrroloxadiazino isoin‐doles 1 by heating in the presence of silica gel. Transformation of the hydroxylactam 6 with acetic acid derivatives led to the esters 7 which gave, after saponification, pyrroloxa(or thia)diazepinoisoindolones 2 by intramolecular cyclization.
Synthesis of pyrimidinones by action of benzamidine on a benzocycloheptenic β‐keto ester
Authors: Muller Nadine , Granet Robert , Lepage Lucette , Krausz Pierre , Laval Jean‐Paul 
Published: March 2009

AbstractThe synthesis of a polycyclic heterocyclic ring system compound, ethyl 7‐hydroxy‐4‐oxo‐2‐phenyl‐4,5‐dihydro‐3H‐benzo[6,7]cyclohepta[1,2‐d]pyrimidine‐6‐carboxylate was carried out by condensation of benzamidine on diethyl 5,9‐dihydroxy‐7H‐benzo[a]cycloheptene‐6,8‐dicarboxylate, after opening and then closure of the seven membered ring.
Benzopyrans. Part 42. Reactions of 4‐Oxo‐4H‐1‐benzopyran‐3‐carbaldehyde with some active methylene compounds in the presence of ammonia
Authors: Ghosh Chandra Kanta , Ray Anirban , Patra Amarendra 
Published: March 2009

AbstractThe title aldehyde 1 in the presence of ammonia gives the pyridine derivatives 9‐11 respectively with acetylacetone, diethyl malonate and ethyl cyanoacetate, and ethyl (or methyl)‐l‐benzopyrano[4,3‐b]pyri‐dine‐3‐carboxylate 22 (or 23) with ethyl (or methyl) acetoacetate. Acetylacetone pretreated with ammonia condenses with 1 giving the fused pyridine 24. Ammonia converts the ester 6 to the pyridine 13 or 14. Chromic acid oxidation of 22 and 23 affords the coumarinopyridines 25 and 26, respectively.
A facile one step synthesis of 1,6 ‐dihydro‐7H‐pyrazolo[4,3‐d]‐pyrimidin‐7‐ones
Authors: Reddy Nalla Ram , Reddy Ghanta Mahesh , Reddy Battu Saida , Reddy Padi Pratap 
Published: March 2009

AbstractA general synthetic approach to pyrazolo[4,3‐d]pyrimidines is reported. Aldehydes, arylideneanilines, carboxylic acids and orthoesters are used as one‐carbon units for bridging the two amino functions of 4‐amino‐1‐alkyl‐3‐propylpyrazole‐5‐carboxamides.
Synthesis of oxazolo[3,2‐b]hetero[1,2,4]thiadiazine S,S‐dioxides
Authors: Vega Salvador , Arranz María Esther , Arán Vicente J. 
Published: March 2009

AbstractSix bromomethyl derivatives of the new 2,3‐dihydrooxazolo[3,2‐b]thieno[3,4‐e][1,2,4]thiadiazine 5,5‐dioxides, 2,3‐dihydrooxazolo[3,2‐b]thieno[2,3‐e][1,2,4]thiadiazine 5,5‐dioxides and 6,7‐dihydrooxazolo‐[3,2‐b]pyrazolo[4,3‐e][1,2,4]thiadiazine 9,9‐dioxides heterocyclic ring systems were synthesized. These compounds are good intermediates for the preparation and development of promising antiviral and psy‐chotropic drugs. The structures of the products are supported by different nmr spectroscopic methods and mass spectrometry.
Synthesis and antimicrobial activity of 3‐(N‐arylamino)‐2‐phenyl‐naphtho[1,3‐d]‐1,2‐oxaphosphole 2‐oxides
Authors: Haranath P. , Anasuyamma U. , Raju C. Naga , Reddy C. Devendranath , Reddy C. Suresh 
Published: March 2009

AbstractThe efficient preparation of cis‐3‐(N‐arylamino)‐2‐phenylnaphtho[1,3‐d]‐1,2‐oxaphosphole 2‐oxides 4 and 5 is described by a three‐component reaction involving phenyldichlorophosphine (2) 1‐hydroxy‐2‐naph‐thaldehyde/1‐hydroxy‐2‐acetonaphthone (1) and different substituted amines (3) in anhydrous benzene. The stereo structure, of the products (4 and 5), as well as the reaction mechanism of the cyclization is discussed. The title compounds (4 and 5) were fully characterized by NMR and mass spectral data. Their anti microbial activity was evaluated