bluuebunny/crossref_metadata_2025_split huggingface dataset:
Physical and chemical properties of hydroxyflavones. IV. Infrared absorption spectra of dihydroxyflavones containing the 5‐hydroxyl group
Authors: Looker J. H. , Hanneman W. W. , Kagal S. A. , Dappen J. I. , Edman J. R. 
Published: March 2009

AbstractSolid state infrared curves (O‐H and C‐H stretching region) are given for 5, n‐dihydroxyflavones, where n is 2′, 3′, 4′, 6, 7 and 8. In chloroform solution spectra of 3,5‐dihydroxyflavone and 3‐hydroxy‐5‐methoxyflavone, the 3‐OH stretching band appears at 3400 and 3334 cm−1, respectively, indicative of a stronger hydrogen bond in the latter substance. Solid state and solution carbonyl bands are presented for twenty‐six flavone derivatives which contain a hydroxyl, methoxyl or acetoxyl group at the 5‐position. The solution spectra (dioxane or carbon tetrachloride) of fourteen flavone derivatives containing a free 5‐hydroxyl group show carbonyl bands at 1655±2 cm−1. Eleven flavones in which the 5‐hydroxyl is blocked (carbon tetrachloride solution) give spectra with flavone carbonyl bands at 1653±3 cm−1. The high resolution chloroform solution spectrum of 3, 5‐dihydroxyflavone possesses a multi‐peaked carbonyl band with midpoint at 1641 cm−1. The chloroform solution spectrum of 3‐hydroxy‐5‐methoxyflavone has a very strong band at 1616 cm−1, with shoulder at 1646 cm−1. Spectral data of this and a previous paper support the postulate that in 4′‐hydroxyflavone the flavone carbonyl oxygen is the donor atom in an intermolecular hydrogen bond. Certain details of synthesis, and analytical data, are given for 3, 5‐dihydroxyflavone.
Reaction of indolylmagnesium bromide and chloromethylpyridines. Synthesis of skatylpyridines and piperidines
Authors: Degraw Joseph I. , Kennedy Jill G. , Skinner W. A. 
Published: March 2009

AbstractThe reaction of indolylmagnesium bromide with the 2‐, 3‐, and 4‐chloromethyl‐pyridines is reported. Methods are described for the preparation of 2‐, 3‐ and 4‐skatylpyridine and 2‐, 3‐ and 4‐skatylpiperidine.
The synthesis and characterization of some 2,1,6‐triaryl and alkylsulfonylhydrazido‐s‐triazines
Authors: Herweh J. E. 
Published: March 2009

Abstract2,4,6‐Trialkyl‐ and triarylsulfonylhydrazido‐s‐triazines (I) have been synthesized by the reaction of cyanuric chloride with a variety of sulfonylhydrazides in a hydrocarbon solvent. The subject compounds (I) were characterized by elemental analysis, molecular weight and spectroscopy.
Novel methylation. III. Methylation of tertiary amines such as pyridine and isoquinoline with alkyl carboxylates
Authors: Kametani Tetsuji , Kigasawa Kazuo , Hayasaka Tetsutaro , Hiiragi Mineharu , Ishimaru Haruhide , Asagi Setsu 
Published: March 2009

AbstractThe alkylation of tertiary amines, namely, 2‐dimethylaminoethanol, triethylamine, pyridine and isoquinoline with various alkyl carboxylates was investigated. This reaction afforded the corresponding quarternary ammonium salts, e.g., methylation of 2‐dimethyl‐aminoethanol with methyl salicylate.
Phenyl substituted dipyrazoles: 1,3‐Dipole addition reactions of sydnones and nitrilimines
Authors: Stille J. K. , Harris F. W. , Bedford M. A. 
Published: March 2009

AbstractA series of phenyl substituted phenylene dipyrazoles has been synthesized by the 1,3‐dipole addition reactions of phenylenedisydnone and phenylenedinitrilimines on phenyl acetylene as well as the reactions of phenylsydnone and phenylnitrilimine on diethynyl‐benzenes. A preliminary study of solvents for the sydnone reaction has been made.
Syntheses and interconversions of some s‐triazolo[3,4‐a]isoquinolines
Authors: Sidhu G. S. , Naqui S. , Iyengar D. S. 
Published: March 2009

Abstracts‐Triazolo[3,4‐a]isoquinoline (II) and its 3‐methyl analogue (III) have been synthesized from 1‐isoquinolylhydrazine (I) by cyclisation with formic and acetic acid. The 3‐hydroxy derivative (IV) has been shown to exist in the lactam form. Methylation with methyl iodide gave the N‐methyl derivative (V). Dimethyl sulphate and diazomethane also led exclusively to the same product. The O‐methyl derivative (IX) could be obtained only through the 3‐chloro compound (VIII). The chlorine atom in VIII undergoes nucleophilic replacement easily. The 3,6‐dichloro derivative (X) has also been prepared. Several interconversions in the series are described. Aryl hydrazones (XVIII) prepared from (I) have been oxidatively cyclised to give 3‐aryl‐s‐triazolo[3,4‐a]isoquinolines (XIX). U.V., I.R. and P.M.R. spectra have been recorded and used for assignment of structures in some cases.
The reduction products of 2‐phenyl‐1,3‐di(4‐pyridyl)‐2‐propanol
Authors: Derieg M. E. , Brust B. , Fryer R. Ian 
Published: March 2009

AbstractA number of chemical modifications of 2‐phenyl‐1,3‐di(4‐pyridyl) ‐ 2 ‐ propanol are described. Dehydration, alkylation and hydrogenation, concomitant and independent, gave a variety of novel compounds. Independent syntheses produced the related compounds X and XVI which were subjected to some of the same reactions. Structural assignments (spectral) were corroborated by the synthesis of common reaction products.
Synthesis of vitamin b6derivatives. II. 3‐Hydroxy‐4‐hydroxymethyl‐2‐methyl‐5‐pyridine acetic acid and related substances
Authors: Tomita Isao , Brooks Houston G. , Metzler David E. 
Published: March 2009

AbstractThe syntheses of 3‐hydroxy‐4‐hydroxymethyl‐2‐methyl‐5‐pyridineacetic and ‐5‐pyridine‐propionic acids and several related compounds are described. Although acid hydrolysis of α4,3‐O‐isopropylidene‐5‐pyridoxic acid gives 5‐pyridoxic acid lactone (α‐pyracin), its higher homolog α4,3‐O‐isopropylidene‐pyridoxylformic acid gave a corresponding free alcohol whose carboxylic acid proton was shown to be exchanged rapidly with the 3‐phenolic and ‐4‐alcoholic ‐ protons in nuclear magnetic resonance studies. Inter‐molecular hydrogen bonding between the side chain carboxylic acid and pyridine nitrogen atoms is suggested in the solid state.
5‐Ethoxy‐3‐(trichloromethyl)‐1,2,4‐oxadiazole
Authors: Narayanan V. L. , Bernstein Jack 
Published: March 2009

Abstract5‐Ethoxy‐3‐(trichloromethyl)‐1, 2, 4‐oxadiazole (V) was synthesized to elucidate the chemistry involved in the preparation of the hitherto unreported alkoxy‐1, 2, 4‐oxadiazoles and to determine the effect of the isosteric replacement of sulfur by oxygen on antifungal activity. Heating the “amino‐oxime” tautomer II of trichloroacetamidoxime with ethyl chloroformate furnished exclusively the O‐acylated product III. The trans configuration of III accounts for its resistance to cyclize under a variety of conditions, in contrast to the general behaviour of acylated amidoximes. Pyrolysis of III at 160° yielded IV which exists in the keto form. Refluxing IV with ethyl iodide in the presence of silver oxide gave an isomeric mixture which was separated by v.p.c. to give V and VI. Compound V retained 60% of the overall activity of the corresponding sulfur analog.
Studies on the benzo[1,2]cyclohepta[3,4,5‐d,e]isoquinoline ring system
Authors: Humber L. G. , Davis M. A. , Thomas R. A. , Otson R. , Watson J. R. 
Published: March 2009

AbstractThe syntheses of various oxidation states of the novel benzo[1, 2]cyclohepta[3, 4, 5‐d, e]‐isoquinoline ring system is described. The ring system was obtained by the Schmidt rearrangement, with exclusive alkyl migration, of 1, 6, 7, 11b‐tetrahydro ‐ 2H ‐ dibenz‐[cd,h]azulen‐2‐one and by a Bischler‐Napieralski reaction of suitable derivatives of 10, 11‐dihydro‐5H‐dibenzo[a, d]cycloheptene ‐ 5 ‐ methylamine. 4, 5, 10, 11 ‐ Tetramethoxy derivatives of the new ring system were best prepared by a Pictet‐Spengler reaction of the appropriate amine.
The synthesis of 2‐aryl‐3‐oxa‐1‐azaspiro [4.4]non‐1‐enes
Authors: Collins Paul W. , Andrako John 
Published: March 2009

AbstractA series of 2‐aryl‐3‐oxa‐1‐azaspiro[4.4]non‐1‐enes was prepared by cyclization of the corresponding β‐acylamino alcohols (V) with thionyl chloride. Structure proofs for the β‐acylamino alcohols and the spiro compounds are given. Infrared and p.m.r. data are reported.
The chemistry of pyrazine and its derivatives. XI. The participation of tetramethylpyrazine in alkylation and aldol‐type reactions
Authors: Chakrabartty Sujit K. , Levine Robert 
Published: March 2009

AbstractUsing sodium amide and phenyllithium as the condensing agents, tetramethylpyrazine has been alkylated with several alkyl halides to give mixtures of alkyltrimethylpyrazines and what are believed to be 2,5‐dialkyl‐3,6‐dimethylpyrazines. Evidence in support of the structures of the dialkylated compounds is presented for the case where the alkylating agent is n‐butyl bromide. A number of carbinols have been prepared by the reaction of tetramethylpyrazine with aldehydes and ketones using phenyllithium as the condensing agent. One of these, 1‐(trimethylpyrazyl)‐2,4‐dimethyl‐2‐pentanol has been dehydrated to 1‐(trimethylpyrazyl)‐2, 4‐dimethyl‐1‐pentene.
The acylation of lepidine
Authors: Baum Burton M. , Levine Robert 
Published: March 2009

AbstractA number of ketones have been prepared in good to high yields by acylating the methyl group of lepidine (III) with a variety of esters using sodium diisopropylamide (II) as the condensing agent. Two ketones, ethyl and isopropyl lepidyl ketone, have been shown to exist in two forms, the keto form and the intermolecular, hydrogen bonded, enolic form.
1,2,3‐benzotriazines. I. The synthesis of some benzimidazo [1,2‐c][1,2,3]‐benzotriazines and naphth[1′,2,(2′,1′):4,5]imidazo[1,2‐c][1,2,3]benzotriazine
Authors: Zaika Laura L. , Joullié Madeleine M. 
Published: March 2009

AbstractA number of substituted benzimidazo[1, 2‐c][1,2,3]benzotriazines were prepared by the diazotization of the appropriate 2‐(o‐aminophenyl)benzimidazoles. Diazotization of 2‐(o‐aminophenyl)naphth[1,2‐d]imidazole yielded a new heterocyclic ring system. Various methods of preparation of 2 ‐ (o‐aminophenyl)benzimidazoles were investigated. The condensation of o‐phenylenediamines with anthranilic acids, in the presence of polyphosphoric acid, provided a convenient route to 2‐(o‐aminophenyl)benzimidazoles but in several cases the products were contaminated with considerable amounts of 6‐(o‐aminophenyl)benzimidazo[1,2 ‐c]quinazolines. 2 ‐ (o‐Aminophenyl)benzimidazoles were also obtained by the catalytic hydrogenation of 2‐(o‐nitrophenyl)benzimidazoles which resulted from the condensation of an o‐phenylenediamine with an o‐nitrobenzaldehyde in ethanol, nitrobenzene or acetic acid. When the condensation was carried out in nitrobenzene, small amounts of 2‐(o‐aminophenyl)benzimidazoles were also formed. The Weidenhagen synthesis, which involves the reaction of an aromatic diamine with an aldehyde in the presence of copper acetate and subsequent decomposition of the cuprous salt of the benzimidazole, yielded 2‐(o‐aminophenyl)benzimidazoles instead of the expected 2‐(o‐nitrophenyl)benzimidazoles when the decomposition was carried out in ethanol. When the cuprous salt was treated with hydrogen sulfide in dilute hydrochloric acid, a mixture of amino‐ and nitrobenzimidazoles resulted. The ultraviolet and infrared spectra of all the compounds prepared were examined.
Synthesis of 6‐substituted pyrimidines by the wittig reaction. I. Via 2‐amino‐4‐hydroxy‐5‐phenylbutylpyrimidine‐6‐carboxaldehyde
Authors: Baker B. R. , Jordaan Johannes H. 
Published: March 2009

AbstractCondensation of isopropyl 6‐phenylhexanoate with ethyl diethoxyacetate followed by guanidine afforded 2 ‐ amino‐6‐diethoxymethyl‐5‐phenylbutyl‐4‐pyrimidinol (VII). Acid hydrolysis of VII gave an excellent yield of 2‐amino‐4‐hydroxy‐5‐phenylbutylpyrimidine‐6‐carboxaldehyde (IV); the latter could be condensed with stabilized Wittig reagents such as carbethoxymethylene triphenyl phosphorane and cinnamylidene triphenyl phosphorane, but not unstabilized Wittig reagents such as carbethoxypropylene or cyano‐propylene triphenyl phosphorane. Reduction of the Wittig products afforded pyrimidines with functionalized side‐chains in the 6‐position such as the 6‐phenylbutyl (XVIII) and 6‐carboxyethyl (XV) derivatives of 2‐amino‐5‐phenylbutyl‐4‐pyrimidinol.
Cyclic imides IV. The reaction of some N‐substituted nitrophthalimides with sodium methoxide
Authors: Caswell Lyman R. , Kao Teresa Ling‐Chun 
Published: March 2009

AbstractTreatment of methyl 4‐nitrophthalimidoacetate (I) with sodium methoxide in refluxing methanol results in a Gabriel‐Colman rearrangement to give 7 ‐ nitro‐4‐hydroxy‐3‐carbomethoxy‐1(2H) ‐ isoquinolone (II). Under the same conditions, N‐substituted 3‐nitrophthalimides (IV) yield N‐substituted 3‐methoxyphthalimides (V).
Analogs of tetrahydrofolic acid. XXXIX . selective bromoacylation of polyfunctional molecules for synthesis of active‐site‐directed irreversible enzyme inhibitors
Authors: Baker B. R. , Santi Daniel V. , Coward James K. , Shapiro Howard S. , Jordaan Johannes H. 
Published: March 2009

AbstractA number of methods for selective bromoacylation of side‐chain amino groups on 2‐amino‐4‐pyrimidinols or 2,4,6‐triaminopyrimidines have been developed for these extremely sensitive products. The choice of method depends upon whether (a) the aminopyrimidine is a stronger base than the amine to be bromoacylated, (b) as weak a base as the amine to be bromoacylated but the amine is more reactive, (c) the amine group to be bromoacylated is a strong aliphatic amine. In case (a) the aminopyrimidine can be protonated to protect it from acylation with an anhydride; in case (b), the reaction with an anhydride is controlled by temperature, stoichiometry, and time of reaction; in case (c), the reaction is selectively controlled by use of the less reactive p‐nitrophenyl esters. Other difficulties were solved such as (a) proper characterization of the products when combustion analyses were unsatisfactory due to polymerization; in these cases a combination of thin layer chromatography, color reactions, and derivatization were employed; and (b) insolubility leading to overreaction on the aminopyrimidine which was solved with partial aqueous systems.
1,2,3‐benzotriazines. II. Reactions of benzimidazo[1,2‐c][1,2,3]benzotriazines and naphth[1′,2′(2′,1′):4,5]imidazo[1,2‐c][1,2,3]benzotriazine
Authors: Zaika Laura L. , Joullié Madeleine M. 
Published: March 2009

AbstractA number of methyl‐ and halogeno‐substituted benzimidazo[1,2‐c][1,2,3]benzotriazines were subjected to a series of hydrolytic cleavages in acid media. The reactions of these compounds with dilute sulfuric acid yielded 2‐(o‐hydroxyphenyl)benzimidazoles. Concentrated hydrochloric acid produced a mixture of 2‐(o‐chlorophenyl)‐ and 2‐(o‐hydroxyphenyl)benzimidazoles. Hydrogen chloride in ethanol caused the formation of 2‐ phenylbenzimidazoles contaminated with small amounts of 2 ‐ (o‐chlorophenyl)benzimidazoles. The benzimidazo[1,2‐c][1,2,3]benzotriazines underwent the Sandmeyer reaction to form 2‐(o‐chlorophenyl)‐ and 2‐(o‐bromophenyl)benzimidazoles in excellent yields. These reactions illustrated the behavior of these 1,2,3‐triazines as internal diazonium compounds. Naphth[1′,2′(2′,1′):4,5]imidazo[1,2‐c][1,2,3]benzotriazine behaved similarly. Bromination of some benzimidazo[1, 2 ‐ c][1,2,3]benzotriazines in aqueous medium yielded bromine‐substituted [1,2‐c][1,2,3]benzotriazines.
Synthesis of a series of isomers of coumestrol
Authors: Spencer R. R. , Knuckles B. E. , Bickoff E. M. 
Published: March 2009

AbstractThree position isomers of the coumestan (2) coumestrol have been synthesized from appropriately substituted flavylium salts. The dimethyl ethers and diacetates of the isomers and several possible monomethyl ethers and their acetates have been prepared.
Thiaindanones III. beckmann rearrangement of oximes
Authors: Aparajithan K. , Thompson A. C. , Sam Joseph 
Published: March 2009

AbstractThe Beckmann rearrangement of 5‐methylthiaindan‐4‐one oximes (I) and thiaindan‐6‐one oximes (IV) proceeds with the migration of the alkyl group to yield dihydrothieno‐pyridones (II and V, respectively). In two instances, the corresponding lactones (VIIa and VIIb) also were isolated. None of the isomeric lactams (X and XI) were isolated from the Beckmann rearrangement reactions. Supporting evidence for the proposed structures is provided.
Stereochemistry of cis‐ and trans‐1‐hydroxy‐1‐phenylquinolizidines
Authors: England James Don , Sam Joseph 
Published: March 2009

Abstractcis and trans‐1‐Hydroxy‐1‐phenylquinolizidines were prepared from 1‐ketoquinolizidine and isolated by column chromatography. Infrared and nuclear magnetic spectral data were utilized for the elucidation of the structures.
Organosilicon compounds I. A novel synthesis of organosilicon substituted furfurals
Authors: Thames Shelby F. , Odom Homer C. 
Published: March 2009

AbstractThe use of the diethylacetal moiety of 2‐furfuraldiethylacetal as a carbonyl blocking agent during n‐butyllithium metalations is described. The synthesis of 5‐silicon substituted furfurals is accomplished for the first time with NMR data being employed as a means of structure proof. Furthermore, the isolation of the uniquely stable organo‐lithium salt, 5‐lithio‐2‐furfuraldiethylacetal, is reported.
The synthesis of 6,7‐dihydro‐5H‐pyrrolo[3,4‐d]pyrimidines. II. 4‐Hydroxy, 4‐mercapto, 2‐amino‐4‐hydroxy and 2,4‐dihydroxy derivatives
Authors: Sheradsky Tuvia , Southwick Philip L. 
Published: March 2009

AbstractSeveral new types of compounds in the 6,7‐dihydro‐5H‐pyrrolo[3,4‐d]pyrimidine series have been prepared. Included are a 6‐acyl derivative unsubstituted in the pyrimidine ring, as well as 4‐hydroxy, 4‐mercapto, 2‐amino‐4‐hydroxy and 2,4‐dihydroxy derivatives. These products were derived directly or indirectly from 4‐cyano‐ or 4‐carbethoxy‐1‐acyl‐3‐amino‐3‐pyrroline intermediates. 3‐Hydroxy, 3‐amino, and 3‐thioformylamino‐1‐acyl‐3‐pyrroline‐4‐thiocarboxamides have been obtained and the 3‐thioformylamino derivatives shown to undergo base‐catalyzed cyclization to close a 4‐mercaptopyrimidine ring.
Irreversible enzyme inhibitors. LXXXIII. Candidate active‐site‐directed irreversible inhibitors of dihydrofolic reductase. VIII. Derivatives of 2,4‐diaminopyrimidine. II
Authors: Baker B. R. , Jordaan Johannes H. 
Published: March 2009

Abstract2,4‐Diamino‐6‐(p‐aminophenethyl)pyrimidines with a 5‐phenylbutyl (XIX) and 5‐(p‐chlorophenyl) (VIII) substituent were synthesized by condensation of the corresponding pyrimidine‐6‐carboxaldehydes (XVI, X) with the Wittig reagent derived from p‐nitro‐benzyl bromide, followed by catalytic hydrogenation. Selective bromoacetylation of VIII and XIX afforded the candidate active‐site‐directed irreversible inhibitors of dihydrofolic reductase, namely, 6‐(p‐bromoacetamidophenethyl)‐2,4‐diaminopyrimidine with a 5‐(p‐chlorophenyl)‐ (IV) and 5‐phenylbutyl‐ (III) substituents. Although III and IV were excellent reversible inhibitors of dihydrofolic reductase, neither showed any inactivation of the enzyme; in contrast, the corresponding 2‐amino‐6‐(p‐bromoacetamidophenethyl)‐5‐phenylbutyl‐4‐pyrimidinol (II) ‐ which differs from III only in the 4‐substituent (NH2 vs. OH) ‐ was an excellent active‐site‐directed irreversible inhibitor of dihydrofolic reductase, but II was a poor reversible inhibitor. Thus the conformations of II and III are most probably different when complexed to dihydrofolic reductase.
Irreversible enzyme inhibitors. LXXXV. On the mode of pyrimidine binding of 5‐alkyl and 5‐arylpyrimidines to dihydrofolic reductase
Authors: Baker B. R. , Lourens Gerhardus J. , Jordaan Johannes H. 
Published: March 2009

AbstractA series of 5‐isoamyl‐ and 5‐(p‐chlorophenyl)pyrimidines substituted with amino, alkylamino, mercapto, benzyloxy, hydroxy, or hydrogen at the 2‐ and 4‐positions and with amino or methyl at the 6‐position have been synthesized for evaluation of the mode of pyrimidine binding to dihydrofolic reductase. The studies were performed in order to determine where a bulky group could be placed on the pyrimidine ring that would still allow good binding; such studies are essential to find a suitable position for placement of a covalent forming group for design of active‐site‐directed irreversible inhibitors. Two classes of candidate compounds have emerged for further study as irreversible inhibitors, namely, 2‐amino‐4‐mercapto‐6‐(p‐bromoacetamidophenylalkyl)‐pyrimidines and 2,4‐diamino‐6‐(p‐bromoacetamidophenylalkyl)aminopyrimidines having a group such as phenyl, phenylbutyl or isoamyl at the 5‐position that can give strong hydrophobic bonding to the enzyme.
Synthesis and properties of 5‐isoxazolethiols
Authors: Adembri G. , Nesi R. 
Published: March 2009

AbstractThe synthesis of a new class of compounds, the 5‐isoxazolethiols, from 5‐chloro‐isoxazoles is described.The chemical properties and tautomeric behaviour in solution and in solid state are deduced from UV and IR spectra. 5‐Ethylthioisoxazoles and 2‐methylisoxazoline‐5‐thiones were also synthesized to support our interpretation.
NMR analysis and synthesis of 6‐ and 8‐C‐methylisoflavones
Authors: Markham K. R. , Mabry T. J. , Rahman W. , Jehan Sardar 
Published: March 2009

AbstractNMR data for eighteen 6‐ and 8‐C‐methylisoflavones provide conclusive evidence that in isoflavones, the C‐8 proton and C‐8 methyl signals occur downfield from the C‐6 proton and C‐6 methyl signals. Other useful NMR correlations and the synthesis of five new C‐methylisoflavones are described.
New aromatic systems having a fused thiazolium ring
Authors: Bradsher C. K. , Lohr D. F. 
Published: March 2009

AbstractThe method developed for the synthesis of thiazolo[3,2‐a]pyridinium salts has been extended to the first synthesis of simple thiazolo[3,2‐a]pyrimidinium, thiazolo[3,2‐a]‐pyrazinium and thiazolo[2, 3‐b]benzo[d]thiazolium salts. No method could be found for the cyclization of 4′‐bromo‐2‐(2‐benzoxazolylthio)acetophenone to the thiazolo[2,3‐b]‐benzoxazolium system.
Preparation of some 2,3,5,6,7,8,8a‐heptahydrothiazolo[3,2‐a]‐s‐triazine‐5,7‐diones
Authors: Penner H. P. , Conklin Alfred R. 
Published: March 2009

AbstractA number of 2‐substituted‐2‐thiazolines have been found to react readily with two moles of isocyanic acid in ethereal solution to give 2, 3, 5, 6, 7, 8, 8a‐heptahydrothiazolo‐[3,2‐a]‐s‐triazine‐5, 7‐diones (IIa‐e). Preliminary reports indicate some activity of these compounds against Walker's carcinosarcoma 256 in rats.
1,2,5‐Selenadiazoles. Synthesis and properties
Authors: Shealy Y. Fulmer , Clayton Joe D. 
Published: March 2009

Abstract4‐Amino‐1, 2, 5‐selenadiazole‐3‐carboxylic acid and 4‐amino‐1, 2, 5‐selenadiazole‐3‐carboxamides have been prepared by ring‐cleavage of [1, 2, 5]selenadiazolo[3, 4‐d]pyrimidin‐7(6H)‐one by basic reagents. The primary amide (III), as well as an N‐alkyl amide, may be produced by the action of a primary amine. Hydrazine reductively cleaves the selenadiazole ring. The preparation of similar 4‐ureido derivatives by ring‐cleavage of [1,2,5]selenadiazolo[3, 4‐d]pyrimidine‐5, 7(4 H, 6H)‐dione has been demonstrated with two examples.N‐Butyl‐4‐ureido‐1, 2, 5‐selenadiazole‐3‐carboxamide is easily hydrolyzed in aqueous base to the corresponding acid, and it has been shown that this reaction proceeds by way of [1, 2, 5]selenadiazolo[3,4‐d]pyrimidine‐5, 7 (4H, 6H)‐dione.The 4‐amino‐1, 2, 5‐selenadiazole‐3‐carboxylic acid derivatives have marked cytotoxic, antibacterial, and antifungal activity.
Reactions of 14‐hydroxy‐14‐azadispiro[5.1.5.2]pentadec‐9‐ene‐7,15‐dione and related compounds. II
Authors: Nightingale Dorothy V. , Johnson James E. 
Published: March 2009

Abstract3 When 11‐diethyl‐ and 3, 11‐di‐n‐propyl‐14‐hydroxy‐14‐azadispiro[5.1. 5.2]pentadec‐9‐ene‐7, 15‐dione (E‐IV and n‐Pr‐IV) are heated with polyphosphoric acid at 55–65°, the 14‐hydroxyl group cyclizes at the 11‐carbon to form E‐VI and n‐Pr‐VI, the structures of which have been established. Compounds P‐IV, i‐Pr‐IV and t‐B‐IV do not cyclize under these conditions.The Beckmann rearrangement of 12‐hydroxy‐12‐azadispiro[4.1.4.2]tridec‐8‐ene‐6, 13‐dione‐6‐oxime (P‐I) with polyphosphoric acid at 40–50° formed only the normal product, P‐II, which could not be cyclized.Compound P‐IV was the only ketone of this series which would add hydrogen cyanide to form a cyanohydrin.