bluuebunny/crossref_metadata_2025_split huggingface dataset:
A novel synthesis of 2,4‐thiophenediamines and their behavior as stable reactive enamines
Authors: Chupp John P. 
Published: March 2009

AbstractReaction of α‐chlorothioacetanilides (1) in refluxing methanol provides a new route to stable, reactive 2,4‐thiophenediamines (2). These materials display interesting chemical and physical properties, based in large part on the interaction of the anilino groups with nuclear substituents alpha to the thiophene sulfur. Thus 2 is easily protonated, with rapid exchange of the 5‐proton, while α‐carbon‐nitrogen cleavage has been observed for the first time during Raney nickel degradation. The susceptibility of the thiophenediamines to electrophilic attack is further demonstrated by facile formation of 3,5‐diamino‐2‐thiophene carboxanilides (3) and 3,5‐diamino‐2‐thienylphenyl ketones (4) from respective reaction of isocyanates, isothiocyanates, and acid chlorides with 2. Certain interesting and unusual spectral characteristics of these compounds, resembling enamines and enaminoketones, are presented and discussed.
Naphthyridine chemistry. XII. Syntheses of N‐oxides
Authors: Paudler William W. , Pokorny David J. , Cornrich Sandra J. 
Published: March 2009

AbstractThe syntheses of the various 1,X‐naphthyridine mono‐ and di‐N‐oxides as well as the 2‐mono‐and 2,7‐di‐N‐oxides of 2,7‐naphthyridine are reported. The PMR spectra of these compounds have been analyzed in detail.
Synthesis of 1,2‐disubstituted naphth [1,2‐d]imidazole‐4,5‐diones
Authors: Carroll F. I. , Blackwell J. T. 
Published: March 2009

AbstractA convenient synthesis of 3‐acylamino‐1,2‐naphthoquinones (I) is presented. The addition of aromatic and aliphatic amines to I followed by exposure to oxygen gives the corresponding 4‐arylamino‐ or 4‐alkylamino‐3‐acylamino‐1,2‐naphthoquinones (II). The addition of 4‐cyclo‐hexylbutylamine to 3‐trichloroacetamino‐1,2‐naphthoquinone took an anomalous course and 1‐(4′‐cyclohexylbutyl)‐3(H)‐naphth[1,2‐d]imidazoline‐2,4,5‐trione (VII) was obtained.Treatment of II with refluxing acetic acid gave 1,2‐disubstituted naphth[1,2‐d]imidazole‐4,5‐diones (III). The reaction was successful with a variety of 4‐substituted amino‐3‐acylamino‐1,2‐naphthoquinones (II) and usually occurred in excellent yield. However, the cyclization of II to III is subject to steric limitation and attempts to cyclize 4‐tert‐butylamino‐3‐acetamino‐1,2‐naphthoquinone to the corresponding imidazole derivative was unsuccessful. The infrared, ultraviolet and nuclear magnetic resonance spectra of I, II, and III are discussed in relation to their structures.
6(5H)‐phenanthridinones. II. Preparation of substituted 6(5h)‐phenanthridinones from 9‐oxofluorenes
Authors: Pan Hsi‐Lung , Fletcher T. Lloyd 
Published: March 2009

AbstractA number of 6(5H)‐phenanthridinones have been conveniently prepared from 9‐oxofluorenes through the Schmidt reaction. It has been found that all amino and nitro 9‐oxofluorenes thus far tried gave substituted 6(5H)‐phenanthridinones with the amino or nitro group situated in the benzene ring attached to the nitrogen of the lactam group. UV and IR spectral data are presented for these compounds.
The synthesis of 3‐deazapyrimidine nucleosides related to uridine and cytidine and their derivatives
Authors: Currie Bruce L. , Robins Roland K. , Robins Morris J. 
Published: March 2009

AbstractCondensation of 2,4‐bis(trimethylsilyloxy)pyridine (1) with 2,3,5‐tri‐O‐benzoyl‐D‐ribofuranosyl bromide (2) gave 4‐hydroxy‐1‐(2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofuranosyl)‐2‐pyridone (3). Deblocking of 3 gave 4‐hydroxy‐1‐β‐D‐ribofuranosyl‐2‐pyridone (3′‐deazauridine) (4). Treatment of 4 with acetone and acid gave 2′,3′‐O‐isopropylidene‐3‐deazauridine (6). Reaction of 4 with diphenylcarbonate gave 2‐hydroxy‐1‐β‐D‐arabinofuranosyl‐4‐pyridone‐O2←2′‐cyclonucleoside (7) which established the point of gylcosidation and configuration of 4. Base‐catalyzed hydrolysis of 7 gave 4‐hydroxy‐1‐β‐D‐arabinofuranosyl‐2‐pyridone (3‐deazauracil arabinoside) (12). Fusion of 1 with 3,5‐di‐O‐p‐toluyl‐2‐deoxy‐D‐erythro‐pentofuranosyl chloride (5) gave the blocked anomeric deoxynucleosides 8 and 10 which were saponified to give 4‐hydroxy‐1‐(2‐deoxy‐β‐D‐erythro‐pentofuranosyl)‐2‐pyridone (2′‐deoxy‐3‐deazauridine) (11) and its α anomer (9). Condensation of 4‐acetamido‐2‐methoxypridine (13) with 2 gave 4‐acetamido‐1‐(2,3,5‐tri‐O‐benzoyl‐β‐D‐ribofuranosyl)‐2‐pyridone (14) which was treated with alcoholic ammonia to yield 4‐acetamido‐1‐β‐D‐ribofuranosyl‐2‐pyridone (15) or with methanolic sodium methoxide to yield 4‐amino‐1‐β‐D‐ribofuranosyl‐2‐pyridone (3‐deazacytidine) (16). Condensation of 13 and 2,3,5‐tri‐O‐benzyl‐D‐arabinofuranosyl chloride (17) gave the blocked nucleoside 22 which was treated with base and then hydrogenolyzed to give 4‐amino‐1‐β‐D‐arabinofuranosyl‐2‐pyridone (3‐deazacytosine arabinoside) (23). Fusion of 13 with 5 gave the blocked anomeric deoxynucleosides 18 and 20 which were deblocked with methanolic sodium methoxide to yield 4‐amino‐1‐(2‐deoxy‐β‐D‐erythro‐pentofuranosyl)‐2‐pyridone (2′‐deoxy‐3‐deazacytidine) (21) and its a anomer 19. The 2′‐deoxy‐erythro‐pentofuranosides of both 3‐deazauracil and 3‐deazacytosine failed to obey Hudson's isorotation rule but did follow the “quartet”‐“triplet” anomeric proton splitting pattern in the 1H nmr spectra.
A synthesis of O‐ethylcularidine (studies on the syntheses of heterocyclic compounds. Part cccxxxiii
Authors: Kametani Tetsuji , Iida Hideo , Kibayashi Chihiro 
Published: March 2009

AbstractIn order to confirm the structure of cularidine (I), O‐ethylcularidine (II) was synthesized and shown to be identical with the naturally occurring O‐ethyleularidine on the basis of NMR spectroscopy and the Rf values.
Chemistry of thienopyridines. IX. Direct nitration of thieno[2,3‐b]pyridine and thieno[3,2‐b] pyridine
Authors: Klemm L. H. , Zell Reinhard , Barnish I. T. , Klemm R. A. , Klopfenstein C. E. , Mccoy D. R. 
Published: March 2009

AbstractThieno[ 2,3‐b]pyridine (I) and thieno[3,2‐b]pyridine (II) were nitrated at C‐3 in ca. 50% yield by means of nitric‐sulfuric acids. Reduction of 3‐nitro‐I (Ia) with tin and hydrochloric acid gave 3‐amino‐I (Ib) (39%), which was converted to 3‐acetylamino‐I (Ic) and to dipyrido[2,3‐b:2′,3′‐d]thiophene (V). Reduction of 3‐nitro‐II (IIa) with iron and acetic acid at 100° gave 3‐acetyl‐amino‐II (IIb) (25%), while use of tin and hydrochloric acid at room temperature gave 2‐chloro‐3‐amino‐II (IIc). Assignments of position of nitration are based on nmr spectral data (which indicate. that substitution occurs in the thiophene ring) and on non‐identities of Ic, IIb, and V with authentic samples of 2‐acetylamino‐I, 2‐acetylamino‐II, and dipyrido[2,3‐b:3′,2′‐d]thiophene (VI), respectively. Results are consistent with reactivity indices for I and II as calculated from simple Hückel Molecular Orbital theory and with observations on nitration and reduction in the isoteric quinoline system.
Dithietanes. Synthesis of N‐substituted 2‐imino‐1,3‐dithietanes and 2‐imino‐1,3‐dithietane hydrochloride
Authors: Addor Roger W. 
Published: March 2009

AbstractThe reaction of diethylphosphoryl isothiocyanate with potassium hydrosulfide gave potassium diethoxyphosphinyldithiocarbamate (3a). This salt, with methylene bromide, afforded 2‐diethoxyphosphinylimino‐1,3‐dithietane (5a) in high yield. In concentrated hydrochloric acid, 5a was hydrolyzed to 2‐imino‐1,3‐dithietane which was isolated as a stable hydrochloride (7). The synthesis of some other N‐Substituted 2‐imino‐1,3‐dithietanes is also described.
The structure of the cations from 2– and 4‐pyrimidones
Authors: Shoffner James P. , Bauer Ludwig , Bell Charles L. 
Published: March 2009

AbstractAn infrared spectral investigation of a number of pyrimidine and pyrimidone hexachloroantimonates is reported. Typical aromatic absorption bands found in pyrimidinium salts were absent in the pyrimidone cations. 2‐And 4‐Pyrimidone hexachloroantimonates, as well as their N‐methyl‐ and N,N'‐dimethyl derivatives, exhibit intense carbonyl absorption bands between 1720–1729 cm−1 (solid state) which corroborates N‐protonation of pyrimidones.
Total synthesis of (±)‐obaberine [studies on the syntheses of heterocyclic compounds. Part CCCXLIX ]
Authors: Kametani Tetsuji , Wakisaka Kikuo , Kigasawa Kazuo 
Published: March 2009

AbstractCyclization of one of two cyclic bisamides (III and IX), followed by reduction and successive methylation, gave our expected bis‐coclaurine derivatives, one of which was identical with O‐methyloxyacanthine, namely natural obaberine (I).
Dihydrocytosines and cytokines from 3‐aminopropionitriles
Authors: Doub Leonard , Krolls Uldis 
Published: March 2009

AbstractThe synthesis of dihydrocytosines 4 from 3‐aminopropionitriles 1 has been broadened and the dihydrocytosines themselves have now been successfully converted to cytosines 9. Unsubstituted 3‐(H, alkyl or aryl) aminopropionitriles (1, X = H) convert with cyanate to 1‐(H, alkyl or aryl)‐1‐(2‐cyanoethyl)ureas (2, X = H), which in turn easily cyclize with anhydrous strong acid or base to 1‐(H, alkyl or aryl)‐5,6‐dihydrocytosines (4, X = H). The 1‐arylaminopropionitriles (1, X = H) which are poorly reactive with cyanic acid combine readily with benzoylureas to form 3‐benzoyl‐1‐(2‐cyanoethyl)‐1‐arylureas (3, X = H). These benzoylureas likewise cyclize with strong acid or base but with simultaneous elimination of the benzoyl moiety to yield the 1‐aryldihydrocytosines 4 (X = H). Amines have successfully been added to 2‐chloroacrylonitrile to yield 2‐chloro‐3‐(amino and substituted amino)propionitriles (1, X = Cl). These 2‐chloropropionitriles also could be converted with cyanate or benzoylisocyanate to ureas and benzoylureas, respectively (1‐(H or alkyl)‐1‐(2‐chloro‐2‐cyanoethyl)ureas (2, X = Cl) or 1‐(H or alkyl)‐1‐(2‐chloro‐2‐cyanoethyl)‐3‐benzoylureas (3, X = Cl). The chlorine substituted ureas were unstable especially to base and to heat but with anhydrous acid were cyclized in high yield to 1‐(H or alkyl)‐5‐chloro‐5,6‐dihydro‐cytosines (4, X = Cl). Direct chlorination of unsubstituted dihydrocytosines 4 (X = H) did not afford these same 5‐chlorodihydrocytosines 4 (X = Cl) under any conditions investigated. 1‐Ethyl‐5,6‐dihydrocytosine (4b) as the cation (hydrobromide) is converted directly in good yield to 1‐ethylcytosine hydrobromide (7) by bromine in nitrobenzene at 140‐160° in a concomitant bromination dehydrobromination reaction. 1‐(Alkyl or aryl)‐5,6‐dihydrocytosines (4, X = H) are halogenated at low temperature in the presence of base to form (N3 or N4)halogenodihydrocytosines (8, R = H). The N‐chlorodihydrocytosines 8 are stable. The N‐bromo and N‐iodo compounds isomerize spontaneously to 5‐halogeno‐5,6‐dihydrocytosines (4, X = Br, I; R = H). The 5‐halogeno‐5,6‐dihydrocytosines 4 (X = Cl, Br, I) whether from cyclization or direct halogenation are readily dehydrohalogenated to the corresponding cytosines 9.
1,4‐Cycloaddition reactions. III. Synthesis of furo[3,2‐c]pyrido[2,3‐g]quinolines, Furo[2,3‐a] [4,7]phenanthrolines, Furo[3,2‐c]pyrrolo[2,3‐g]quinolines, Furo[3,2‐c]pyrrolo[3,2‐g]quinolines, and Furo[3,2‐c]furo[2′,3′:4,5]pyrido[2,3‐g]quinolines from 2,3‐dihydro‐5‐methylfuran and schiff bases
Authors: Perricone S. C. , Worth Donald F. , Elslager Edward F. 
Published: March 2009

AbstractThe 1,4‐cycloaddition of 2,3‐dihydro‐5‐methylfuran (II) to 1‐acetyl‐1,2,3,4‐te trahydro‐6‐[(p‐hydroxybenzylidene)amino]quinoline (VIII) in the presence of boron trifluoride gave two pairs of epimers, namely dl‐10‐acetyl‐2,3,3a,4,5,7,8,9,10,11b‐decahydro‐4‐(p‐hydroxyphenyl)‐11b‐methylfuro[3,2‐c]pyrido[2,3‐g]quinoline (IXa and b) and dl‐8‐acetyl‐2,3,3a,4,5,8,9,10,11,‐11c‐decahydro‐4‐(p‐hydroxyphenyl)‐11c‐methylfuro[2,3‐a][4,7]phenanthroline (Xa and b). dl‐9‐Acetyl‐3,3a,4,5,7,8,9,10b‐octahydro‐4‐(p‐hydroxyphenyl)‐10b‐methyl‐2H‐furo[3,2‐c] pyrrolo‐[2,3‐g]quinoline (XIIIa) was the predominant product isolated from the reaction of II with 1‐acetyl‐5‐[p‐(hydroxybenzylidene)amino]indoline (XII). When 1‐acetyl‐6‐[(p‐hydroxybenzylidene)amino]indoline (XVI) was treated with 2,3‐dihydro‐5‐methylfuran (II), two epimers of dl‐7‐acetyl‐3,3a,4,5,7,8,9,10b‐octahydro‐4‐(p‐hydroxyphenyl)‐10b‐methyl‐2H‐furo[3,2‐c]pyrrolo[3,2‐g]quinoline (XVIIa and b) were obtained. dl‐2,3,3a,4,5,6b,8,9,9a,10,11,12b‐Dodecahydro‐4,10‐bis(p‐methoxyphenyl)‐6b,12b‐dimethylfuro[3,2‐c]furo[2′,3′:4,5]pyrido[2,3‐g]quinoline (XX) was formed when 2,3‐dihydro‐5‐methylfuran was allowed to react with N,N'‐bis(p‐methoxybenzylidene)‐p‐phenylcnediamine (XIX). Structure assignments were made from NMR spectra. None of the compounds exhibited appreciable biological activity.
2H‐1,4‐benzothiazines from the reaction of 2‐aminoethanethiol with nascent 4‐methyl‐o‐benzoquinone
Authors: Prota G. , Petrillo O. , Santacroce C. , Sica D. 
Published: March 2009

Abstract4‐Methyl‐o‐benzoquinone, generated oxidatively, reacts readily with 2‐aminoethanethiol giving 5‐hydroxy‐7‐methyl‐1,3,4‐dihydro‐2H‐1,4‐benzothiazine (I) or 5‐oxo‐7‐methyl‐8‐(2‐hydroxy‐4‐methylphenoxy)‐3,5‐dihydro‐2H‐1,4‐benzothiazine (VIII), depending on the conditions under which the reaction is performed. Chemical and spectral (uv, ir, nmr and ms) evidence for the assigned structures, as well as the course of the above mentioned reaction is described.A study of the behaviour of compound VIII in the presence of acids and alkalies is also reported.
Reaction of cis‐2,3‐dioctylaziridine with carboxylic acids
Authors: Maerker G. , Haeberer E. T. , Donahue E. T. , Foglia T. A. 
Published: March 2009

AbstractA series of aliphatic and aromatic carboxylic acids reacted with 2,3‐dioctylaziridine to yield β‐hydroxyalkyl amides in 69–89% yields and 2‐substituted 4,5‐di‐n‐octyl‐δ2‐oxazolines in amounts ranging from traces to 12% of the theoretical. No correlation could be found between carboxylic acid strength and either hydroxyamide or δ2‐oxazoline yields. Solvents affected the product distribution.
2,5‐diphenyl‐3‐morpholinofuran and its 2‐hydro, 2‐bromo and 2‐hydroxymorpholinofurylium salts
Authors: Lutz R. E. , Hankins W. M. , Hankins M. G. , Welstead W. J. , Dickerson C. L. 
Published: March 2009

Abstract2,5‐Diphenyl‐3‐morpholinofuran (1) reacts with bromine and trifluoroacetic acid, giving respectively 2‐bromo and 2‐hydro furylium salts (2,3). The 2‐hydroxy furylium bromide (4) was obtained by reaction of cis‐morpholino‐1,2‐dibenzoylethylene (5) with hydrogen bromide. The nmr spectra of these salts show differences between the two morpholino dimethylene moieties of each caused by restricted rotation at the 3‐immonium group. Chemical relationships studied include reductions to the morpholinofuran, conversions to 3‐furanones, and the slow reaction of morpholinodibenzoylethylene with phenylmagnesium bromide to give cis‐dibenzoylstyrene (13).
Proton magnetic resonance studies of compounds with bridgehead nitrogen atoms. XIV .: The influence of an axial 5‐methyl group on the chemical shifts of C2 methylene protons in 1,3‐heterosystems
Authors: Crabb T. A. , Chivers P. J. , Jones E. R. , Newton R. F. 
Published: March 2009

AbstractThe shielding of a C‐2 axial proton by an axial C‐5 methyl group in 1,3‐heterocyclic systems is described and explained in terms of conformational distortion.
Pyridazines. XXXIV. Electron‐impact induced fragmentation of some s‐triazolo[4,3‐b] pyridazines, tetrazolo[1,5‐b] pyridazines and related compounds
Authors: Pirc V. , Stanovnik B. , Tišler M. , Marsel J. , Paudler W. W. 
Published: March 2009

AbstractMass spectra of several 4‐triazolo[4,3‐b]pyridazines and tetrazolo[1,5‐b]pyridazines were examined in order to establish their fragmentation patterns. Two distinct patterns could be observed upon electron impact of s‐triazolo[4,3‐b]pyridazines and tetrazolo[1,5‐b]pyridazines. Azidotetrazolopyridazines show a loss of six nitrogens. This can be accounted for by a path proceeding via a molecular ion with a bis‐tetrazolo structure.
The synthesis of certain 4‐mono‐ and 4,7 dihydroxy‐1,10‐phenanthrolines
Authors: Case Francis H. 
Published: March 2009

AbstractAminocrotonates and cinnamates formed by the action of ethyl acetoacetate and ethyl benzoylacetate on substituted 8‐aminoquinolines have been cyclized to 4‐hydroxy and 4,7‐dihydroxy‐1,10‐phenanthrolines.
Mass spectra of some aminonaphthyridines and aminoquinolines
Authors: Brown Ellis V. , Plasz Andrew C. , Mitchell Stanley R. 
Published: March 2009

AbstractThe mass spectra of all the aminoquinolines, the 2–, 3– and 4‐amino‐1,5‐naphthyridines, some amino‐1,6‐naphthyridines, and two amino‐1,8‐naphthyridines with methyl substituents are reported. The major fragment in the aminoquinolines is formed by the loss of HCN from the molecular ion. The most abundant fragment in the aminonaphthyridines is formed by the loss of HCN from the molecular ion except in the 2‐amino‐1,5‐naphthyridine isomer. In both 1,8‐naphthyridine isomers investigated, the loss of C2H2 is an alternate fragmentation pathway of significance. In all of the compounds investigated, the loss of the primary amino group from the molecular ion was found to be an insignificant fragmentation.
Crystal and molecular structure of cis 11‐(p‐iodobenzenesulfonyl)‐11‐azabicyclo[8.1.0]undecane
Authors: Zacharis H. , Trefonas L. M. 
Published: March 2009

AbstractThe crystal and molecular structure of the title compound was determined by single‐crystal x‐ray diffraction techniques. The compound crystallizes in the orthorhombic space group Pca21, with four molecules in a unit cell of dimensions a = 17.552 ± .003, b = 8.235 ± .0008 and c = 11.914 ± .001 Å. The structure was solved by the heavy atom method and refined by full matrix least squares to a final value of R = 0.055 for the 740 independently measured, statistically significant reflections. The conformation of the cyclodecane ring in the bicyclic system differs from the idealized cyclodecane ring based on conformational studies and previous x‐ray determinations of simpler systems. The differences in conformation are discussed.
Azabicyclo chemistry II. Synthesis of 1,5‐methano‐2,3,4,5‐tetrahydro‐1H‐2‐benzazepines. B‐norbenzomorphans
Authors: Mokotoff Michael , Jacobson Arthur E. 
Published: March 2009

AbstractThe syntheses of the B‐norbenzomorphans, 1,5‐methano‐2,3,4,5‐tetrahydro‐1H‐2‐benzazepine (1a) and itsN‐methyl derivative (Ib) were accomplished. Phenylsuccinic anhydride (III) was cyclized to 3‐carboxy‐1‐indanone (IVa), which was converted by the Arndt‐Eistert method to the homologous methyl indanone‐3‐acetate (V). One experiment in the synthesis of V led to the by‐products 3‐carboxamido‐1‐indanone (IVd) and 3‐(N‐methylcarboxamido)‐1‐indanone (IVe), identified by physical and chemical means. Methyl 1‐aminoindan‐3‐acetate (VII) was prepared by catalytic reduction of methyl indanone‐3‐acetate oxime (VI). Hydrolysis of VII afforded 1‐aminoindan‐3‐acetic acid (VIII), which was cyclized with dicyclohexylcarbodiimide to 1,5‐methano‐2,3,4,5‐tetrahydro‐1H‐2‐benzazepin‐3‐one (IX). Reduction (lithium aluminum hydride) of IX gave amine Ia which was then methylated to Ib. The mass spectral fragmentation patterns of IX and Ia are discussed.
The formation of the indolizino[1,2‐c]quinolinium system by a novel nucleophilic reaction
Authors: Bradsher Charles K. , Burnham Weldon S. , Zinn Mary F. 
Published: March 2009

Abstract2‐Methyl‐3‐(2‐pyridyl)quinoline (1) with a bromomethyl ketone or ethyl bromoacetate yields 6‐methyl‐12‐acylindolizino[1,2‐c]quinolinium bromides (5–9). The acyl derivatives can be deacylated in acid yielding 6‐methyl indolizino[1,2‐c]quinolinium salts (4). Benzoylation of 4 yields the 12‐benzoyl derivative (6).The deacylation product (4) has been synthesized from 2‐acetamidophenacyl bromide (10) and 2‐pyridylacetone (12).
Pyrrolopyrimidine nucleosides. VI. Synthesis of 1,3 and 7‐β‐D‐ribofuranosylpyrrolo[2.3‐d] pyrimidines via silylated intermediates
Authors: Tolman Richard L. , Tolman Glen L. , Robins Roland K. , Townsend Leroy B. 
Published: March 2009

AbstractThe ribosylation of several silylated pyrrolo[2,3‐d]pyrimidines by the Wittenberg procedure has produced 1,3 and 7‐ribosylpyrrolo[2,3‐d]pyrimidine derivatives in high yield. Structure assignments have been made on the basis of the ultraviolet spectra of model compounds and further confirmed by chemical conversion to derivatives of established structure. A convenient ribosylation procedure utilizing silver oxide, a halosugar, and a silylated pyrrolo[2,3‐d]pyrimidine derivative in acetonitrile has been described.
Studies on the syntheses of azole derivatives. Part II . Syntheses of N‐(1‐ or 2‐Substituted)indazolones via Diazotization
Authors: Kametani Tetsuji , Sota Kaoru , Shio Masahisa 
Published: March 2009

AbstractSyntheses of 2,5‐disubstituted‐indazolones (Ixa–g) and 3‐hydroxy‐1‐substituted‐1H‐indazoles (XIVa,b) were achieved by diazotization of 2‐benzoylaniline (VIa–g) and N‐benzoylhydrazine (XIIa–c), respectively.
Studies on the syntheses of azole derivatives. Part III. Syntheses of 1‐Phenyl‐Δ2‐1,2,4‐triazolin‐5‐one and 4‐Phenyl‐Δ2‐1,3,4‐oxadiazolin‐5‐one Derivatives by Fusion of 1‐Phenyl‐2‐acylhydrazine with Urea
Authors: Kametani Tetsuji , Sota Kaoru , Shio Masahisa 
Published: March 2009

AbstractFusion of 1‐phenyl‐2‐acylhydrazine (III) with urea gave Δ2‐1,2,4‐triazolin‐5‐one and Δ2‐1,3,4‐oxadiazolin‐5‐one derivatives together with various by‐products. Furthermore, various derivatives were synthesized for the purpose of examination in a pharmacological screening test.
Synthesis of 4‐azatricyclo[4.3.1.13,8] undecane (4‐azahomoadamantane)
Authors: Narayanan V. L. , Setescak L. 
Published: March 2009

AbstractEfficient routes for the synthesis of 4‐azahomoadamantane (V) via the Beckmann and Schmidt rearrangements are described. The lactam III is unusual in that it forms a stable crystalline hydrochloride IV.
Preparation and some reactions of 3‐oxazoline N‐oxides
Authors: Hansen Gary R. , Boyd Robert L. 
Published: March 2009

AbstractSubstituted 3‐oxazolines react with m‐chloroperoxybenzoic acid to give the corresponding 3‐oxazoline N‐oxides. These heterocyclic nitrones underwent molecular rearrangements, but would not react with 1,3‐cyclo‐addition type reagents.
The preparation of 1,2,4‐Triazines and 1,2,4‐Triazolines from substituted carboxamide hydrazones
Authors: Case Francis H. 
Published: March 2009

AbstractSubstituted carboxamide hydrazones have been condensed with 2,3‐butanedione and with glyoxal to form 1,2,4‐triazines; with benzaldehyde and pyridine‐2‐carboxaldehyde to yield 1,2,4‐triazolines.
Condensation of pyridoxal with the methyl ester of glycine
Authors: Korytnyk W. , Ahrens H. 
Published: March 2009

AbstractCondensation of pyridoxal with the methyl ester of glycine gave the aminocoumarin analog 3‐amino‐8‐rnethyl‐2‐oxo‐2H‐pyrano[2,3‐c]pyridine‐5‐methanol (III), and not the expected aldimine. The structure of the compound was deduced by independent synthesis and by comparing its NMR spectrum with that of 3‐aminocoumarin. The new reaction provides routes for the synthesis of α4‐pyridoxylideneglycine and α4‐pyridoxyloxoacetic acid derivatives. It may also provide a model for irreversible inactivation of vitamin B6 in biochemical systems.
1,2,4‐Triazoles. XXV. The effect of pyridine substitution on the isomerization of s‐Triazolo[4,3‐a] pyridines into s‐Triazolo[1,5‐a] pyridines
Authors: Potts K. T. , Surapaneni C. R. 
Published: March 2009

AbstractThe isomerization of s‐triazolo[4,3‐a]pyridines into s‐triazolo[1,5‐a]pyridines is greatly facilitated by electron withdrawing nitro substituents in the pyridine ring and retarded by electron donating amino groups.
Investigation of some tetrazole derivatives of 1,8‐naphthyridines
Authors: Carboni S. , Da Settimo A. , Ferrarini P. L. , Ciantelli P. L. 
Published: March 2009

AbstractSeveral tetrazole derivatives have been prepared from 7‐amino‐2‐hydroxy‐3‐phenyl‐1,8‐naphthyridine (Id). Evidence is presented to demonstrate that the tetrazole ring structure is the dominant species in the solid state and in alkaline solution while the open‐chain azido form dominates in acidic solution. In addition it has been shown that the presence of a phenyl group in a position adjacent to the tetrazole nucleus apparently stabilizes the tetrazole ring.