bluuebunny/crossref_metadata_2025_split huggingface dataset:
A novel oxamide rearrangement
Authors: Peet Norton P. , Sunder Shyam , Barbuch Robert J. 
Published: March 2009

AbstractAn efficient, base‐induced rearrangement of 2‐[(1,2‐dioxo‐2‐(methylamino)ethyl)phenylamino]benzoic acid methyl ester (7a) to the isomeric 2‐[(1,2‐dioxo‐2‐(phenylamino)ethyl)methylamino]benzoic acid methyl ester (27a) is described. This novel rearrangement must proceed through a spiro intermediate wherein benzoate is acting as a Michael receptor. When 2‐[(1,2‐dioxo‐2‐(methylamino)ethyl)methylamino]benzoic acid methyl ester (28)‐an oxamide which would produce a degenerate spiro intermediate — was subjected to rearrangement conditions, the product obtained was 1,3‐dimethyl‐2,4‐(1H,3H)quinazolinedione (29). This latter transformation may have proceeded via a benzodiazepinetrione intermediate.
Reactions of 2‐acyl‐1,3‐indandiones
Authors: Lemke Thomas L. , Parker George R. 
Published: March 2009

Abstract2‐Pivaloyl‐1,3‐indandione reacts with thiosemicarbazide in aqueous base, through two successive retro‐Claisen reactions, to yield 1‐hydroxy‐4‐methylphthalazine. The mechanism of this reaction is described. Under similar conditions, 2‐benzoyl and 2‐acetyl‐1,3‐indandione, did not undergo the same reaction, a steric factor is considered.
Reactions of o‐aminonitriles with isocyanates. 1. A two‐step synthesis of 2,6‐dihydroimidazo[1,2‐c]quinazolin‐5‐(3H)one
Authors: Papadopoulos Eleftherios Paul 
Published: March 2009

AbstractThe reaction of anthranilonitrile with 2‐chloroethyl isocyanate yields 2‐[3‐(2‐chloroethyl)ureido]benzo‐nitrile (6) which, upon heating, or treatment with base, undergoes a double cyclization to form 2,6‐dihydroimidazo[1,2‐c]quinazolin‐5‐(3H) one (8) in excellent yield. When heated with hydrochloric acid, 6 is converted initially into 2‐(2‐chloroethylamino)‐4H‐[3,1]benzoxazin‐4‐one (18) and further into 3‐(2‐chloroethyl)‐2,4‐(1H,3H)quinazolinedione (15). The acid‐catalyzed reaction of 2,3‐dihydro‐5H‐oxazolo[2,3‐b]quinazolin‐5‐one (14) with nucleophilic reagents yields 3‐substituted 2,4‐(1H,3H)quinazolinediones.
Preparation of 4‐aryl‐1,2,3,4‐tetrahydro‐3,3‐dimethylisoquinolines and 1,2,3,4‐tetrahydro‐3,3‐dimethyl‐4‐phenylbenz[h]isoquinolines
Authors: Bobowski George , Gottlieb Jeffrey M. , West Barbara 
Published: March 2009

AbstractSynthetic procedures to prepare a number of 4‐aryl‐1,2,3,4‐tetrahydro‐3,3‐dimethylisoquinolines and their benzo‐homogues 3 through a series of intermediates are described. The condensation of α‐(1‐amino‐1‐methylethyl)arylmethanols 5 with arylaldehydes 6 gave imino derivatives 7 which on reduction with borohydride gave secondary amines 8. The treatment of 8 with mineral acids gave the target compounds 3. Biological activities of 3 are briefly discussed.
The synthesis of 5,6‐dimethoxycyclopentano[h]‐isoquinoline and derivatives
Authors: Solomons William E. , Mathison Ian W. 
Published: March 2009

AbstractThe synthesis of the previously unreported 5,6‐dimethoxycyclopentano[h]isoquinoline (1) by way of a Pomeranz Fritsch ring closure of the diethyl acetal of 4,5‐dimethoxy‐7‐indanylidene aminoacetaldehyde (3) is reported. Acetylation of the N‐oxide of 1 yielded the corresponding N‐acetyl‐1‐isoquinolone, which readily converted to the 1‐isoquinolone on exposure to atmospheric moisture. Several diesters of the dihydroxy analog of 1 are reported.
Identification ofN‐methylpyrazole analog isomers by13C NMR
Authors: Agnew Marc N. , Bauer Victor J. , Effland Richard C. 
Published: March 2009

AbstractUsing severalN‐methyl pyrazole analogs the utility of13C nmr in determining isomeric structures was examined. The chemical shift assignments of the pyrazole carbons and thus the isomeric structures were determined using a combination of proton coupled and proton decoupled13C nmr spectra.
Merocyanine dyes from 4‐dicyanomethylene‐2,6‐dimethyl‐4H‐pyran
Authors: Van Allan J. A. , Reynolds G. A. 
Published: March 2009

AbstractNeutral dyes were prepared by reacting 1‐ethyl‐2[2‐(N‐methylanilino)vinyl]quinolinium iodide with 4‐dicyanomethylene‐2,6‐dimethyl‐4H‐pyran and then condensing the resulting product with an aromatic aldehyde.
Studies in the heterocyclic series. XVIII. Utilization of 4‐aminopyrimidine chemistry in 1,4,7,9‐tetraazabenzo[b]phenothiazine synthesis
Authors: Okafor Charles O. 
Published: March 2009

AbstractThe synthesis of 1,4,7,9‐tetraazabenzo[b]phenothiazine ring system from 4‐aminopyrimidine is reported. This new heterocyclic ring was obtained by converting a 4‐aminopyrimidine to the corresponding 5‐thiocyanato derivative followed by hydrolysis and subsequent treatment with 2,3‐dichloroquinoxaline. Several derivatives were obtained by using suitable substituted starting materials. Nitration with mixed nitric and sulfuric acids gave the corresponding 13‐nitro derivatives. Spectral analyses are in agreement with the assigned structures.
Reaction of alkoxyuridines with ammonia
Authors: Mathews Robert A. , Stöhrer Gerhard 
Published: March 2009

Abstract2‐Alkoxy‐ and 4‐alkoxyuridines were converted into isocytidine and cytidine by reaction with ammonia at room temperature. Reaction with hydrogen sulfide produced 2‐thio‐ and 4‐thiouridine but the reaction was incomplete. The reaction may be helpful in the identification of alkylated pyrimidine nucleosides in DNA.
Synthesis of 11‐deoxy‐5,6‐didehydro‐13,14‐dihydro‐8‐azaprostaglandin E1
Authors: Zoretic P. A. , Jardin J. , Angus R. 
Published: March 2009

AbstractThe synthesis of 11‐deoxy‐5,6‐didehydro‐13,14‐dihydro‐8‐azaprostaglandin E1 is reported. The effects of the 8‐aza‐PGE1 analog on human bronchial muscle and its antisecretory activity is also reported.
Condensation of 2‐aminophenols and α‐dicarbonyl compounds. Part 4. Dibenzoxazolines substituted with heterocycles
Authors: Belgodere E. , Bossio R. , Parrini V. , Pepino R. 
Published: March 2009

AbstractThe tautomeric structure of 2,2′‐dibenzoxazolines 2′‐substituted with heterocycles was investigated by ir, pmr and uv spectroscopy.
N‐Alkyl derivatives of trans‐6,7‐dihydroxy‐1,2,3,4,4a,5,10,10b‐octahyrobenzo[g]quinoline A congener of apomorphine lacking the non‐oxygenated aromatic ring
Authors: Cannon Joseph G. , Lee Teresa , Beres James A. , Goldman H. Duane 
Published: March 2009

AbstractA synthetic sequence leading to the title compounds began with methyl 5,6‐dimethoxy‐2‐tetralone‐3‐carboxylate and involved a multi‐step construction of the heterocyclic ring. The trans‐fused isomer was isolated from the cyclization step. However, the possibility of formation of some cis‐fused isomer cannot be precluded.
Synthesis of (4S,9aS)‐hexahydro‐4‐methyl‐1H,5H‐pyrrolo[2,1‐c][1,4]‐thiazepine‐1,5‐dione, A potent angiotensin converting enzyme inhibitor
Authors: Kim Dong Han 
Published: March 2009

AbstractSynthesis of (4S,9aS)‐hexahydro‐4‐methyl‐1H,5H‐pyrrolo[2,1‐c][1,4]thiazepine‐1,5‐dione, an orally active potent angiotensin converting enzyme inhibitor is described.
Deoxygenation and X‐ray photoelectron studies on some quinoxalines and their N‐oxides
Authors: El‐Abadelah Mustafa M. , Anani Ali A. , Khan Zahida H. , Hassan A. M. , Katrib Ali 
Published: March 2009

AbstractDeoxygenation results of some quinoxaline dioxides with phosphorous trichloride are presented and compared with previous deoxygenations with other reagents. Differentiation between isomeric quinoxaline oxides using X‐ray photoelectron spectroscopy is also discussed.
A convenient route to α‐amido‐β‐lactams
Authors: Bose Ajay K. , Manhas M. S. , Gala K. , Sahu D. P. , Hegde V. 
Published: March 2009

AbstractDedicated to Professor John C. Sheehan on the occasion of his sixty‐fifth birthday.A method for the synthesis of α‐amido‐β‐lactams without the intermediacy of an α‐amino‐β‐lactam is described. The appropriate β‐keto ester is used for preparing a vinylamino β‐lactam via a “Dane salt” by a previously reported method. Oxidation with ruthenium tetroxide and periodic acid of this product leads directly to the desired “V”, or “G” or analogous α‐amido side chain.
Quinazolines and 1,4‐Benzodiazepines. XC. 2‐Aminoimidazo[1,5‐a][1,4]benzodiazepin‐1‐ones and derivatives
Authors: Walser Armin , Flynn Thomas 
Published: March 2009

AbstractThe addition of diethyl azodicarboxylate to an electron rich double bond was employed as the key step for the preparation of the title compounds. Novel tetracyclic [1,2,4]triazino[1′,6′:3,4]imidazo[1,5‐a][1,4]benzodiazepines were accessible from these 2‐aminoimidazo[1,5‐a][1,4]benzodiazepin‐1‐ones.
Synthesis and mass spectral studies of a coumarin analog of chloramphenicol
Authors: Bevinakatti Hanamanthsa S. , Badiger Virupax V. 
Published: March 2009

AbstractPreparation of dl‐threo‐2‐dichloroacetamido‐1‐(3‐coumarinyl)propane‐1,3‐diol (7) is discussed. The structures of the final compound (7) as well as its two precursors (5 and 6) were confirmed by ir and nmr studies. Because of the larger side chain, the coumarin analog (7) breaks down in a well defined manner upon electron impact. Its mass spectral fragmentation patterns are described.
Synthesis of heterocycles. Part II. New routes to acetylthiadiazolines and alkylazothiazoles
Authors: Eweiss N. F. , Osman A. 
Published: March 2009

AbstractMethylglyoxalyl chloride arylhydrazones (III) react with an ethanolic solution of thiourea to give 2‐amino‐4‐methyl‐5‐arylazothiazoles (XII) instead of the expected 2‐acetyl‐4‐aryl‐5‐imino‐Δ2‐1,3,4‐thiadiazolines (V) which were obtained from III and potassium thiocyanate. 3‐Thiocyanato‐2,4‐pentanedione (IV) coupled with diazotized anilines to give V. The postulated routes to formation of V and XII from III are given. Nitrosation of V gave the corresponding N‐nitroso derivatives (VI) which decomposed upon refluxing in dry xylene to give 2,4‐disubstituted‐Δ2‐1,3,4‐thiadiazolin‐5‐ones (VII). Boiling of either V or VI with hydrochloric acid gave the hydrochloride salt (VIII). The thiadiazolines V gave the respective N‐acyl derivatives (IX) and (X) with acetic anhydride and benzoyl chloride in pyridine.
Syntheses of 2‐arylimidazole derivatives through annelations employing benzylamines
Authors: Veronese A. C. , Cavicchioni G. , Servadio G. , Vecchiati G. 
Published: March 2009

AbstractAnnelations of benzylamines with hydroximino derivatives of pentane‐2,4‐dione or of alkyl acetoacetates, acetoacetamides, and acetoacetanilides, afford imidazole derivatives and provide easy incorporation of the benzylic carbon and nitrogen in the heterocycle. The limits of the reaction have been explored.
A novel pentacyclic pyridine dilactone. 7‐methyl[1]benzopyrano[4,3‐d][1]benzoxacino[4,3‐b]pyridine‐6,16‐dione
Authors: Rajyalakshmi K. , Srinivasan V. R. 
Published: March 2009

AbstractWhen equimolar quantities of salicylaldehyde 2 and ethyl 3‐amino‐2‐butenoate 3 or its constituents (ethyl 3‐oxobutanoate and ammonia) were refluxed on a steam‐bath for 6 hours with a trace of acetic acid, two products, a pentacyclic pyridine dilactone 4 and 3‐acetyl coumarin 5, resulted in 15% and 45% yields, respectively. The structure of 4 was elucidated as 7‐methyl[1]benzopyrano[4,3‐d][1]benzoxacino[4,3‐b]‐pyridine‐6,16‐dione on the basis of its spectral data. The mechanism of its formation has been discussed. The reaction has been extended to three more substituted salicylaldehydes.
Direct nitration of aldehyde arylhydrazones and the use of the products in the synthesis of some heterocyclic compounds
Authors: Shawali Ahmad S. , Hassaneen Hamdi M. , Sherif Sherif M. 
Published: March 2009

AbstractDirect nitration of substituted benzaldehyde p‐nitrophenylhydrazones 1 gave α‐nitroarylidene‐p‐nitrophenylhydrazines 2. Reactions of 2 with nucleophiles result in displacement of the nitrite. Treatment of 2 with potassium thiocyanate gave 5‐imino‐1,3,4‐Δ2‐thiadiazolines 10. Reactions of 2 with carbanions of active methylene compounds yielded the pyrazole derivatives 15–20. 1,3‐Dipolar cycloadditions of 2 onto acrylonitrile and benzalacetophenone afforded the expected cycloadducts 21 and 22, respectively.
Polyazasteroids. III. 1,2,4‐triazolo[3,4‐a]benzo[f]isoquinoline. Synthesis of the diazaphenanthrene alkaloid perlolidine and its 1,8‐phenanthroline isomer
Authors: Lalezari I. , Nabahi S. 
Published: March 2009

AbstractA series of 1,2,4‐triazolo[3,4‐a]benzo[f]isoquinolines, which constitutes a new class of polyazasteroidal compounds, were synthesized. A simple synthesis of the diazaphenanthrene alkaloid perlolidine as well as 1,8‐phenanthrolin‐7‐(8H)one is reported.
The synthetic utility of heteroaromatic azido compounds. Part VI. Preparation of some 1H‐1,2,3‐triazolo[1,5‐a]thieno[3,2‐d]pyrimidines
Authors: Westerlund Christer 
Published: March 2009

AbstractSome 1,2,3‐triazolo[1,5‐a]thieno[3,2‐d]pyrimidines have been prepared by the reaction of active methylene nitriles with 3‐azido‐2‐substituted thiophenes. Thus, for example the 3‐carboxy derivative 5 was prepared by condensation of 3‐azido‐2‐formylthiophene dimethyl acetal (1) with ethyl cyanoacetate, followed by intramolecular cyclization. Decarboxylation of 5 led to the unsubstituted parent compound 6. The structure of the triazole‐fused compounds is discussed.
The chemistry of 2H‐1,3‐benzoxazine‐2,4‐(1H)dione (isatoic anhydride). 8. A one step synthesis of the quinindoline ring system and related compounds
Authors: Coppola Gary M. 
Published: March 2009

AbstractThe reaction between N‐substituted isatoic anhydrides and the carbanion generated from 3‐methylthio‐oxindole to produce the quinindoline ring skeleton is discussed. Analogous reactions of azaisatoic anhydride 6 and tricyclic anhydride 8 produces the 4‐aza analog 7 and pentacycle 9. Some spectral data is also described.
O‐ethyl thiocarbamates. A convenient route to 2‐aryliminoimidazolidines
Authors: Reynaud Pierre , Brion Jean‐Daniel , Davrinche Catherine , Dao Phan‐Chi 
Published: March 2009

AbstractThe reaction of N‐aryl thionocarbamates and ethylenediamine lead to the corresponding 2‐arylimino‐imidazolidines, whose structure in pharmacology is well known. But, the behaviour of the N‐alkyl thionocarbamates is quite different under operative conditions and these compounds afford with ethylenediamine, to 2‐(2′‐aminoethylamino)‐Δ2‐imidazoline, according to a mechanism which is discussed.
Structure elucidation of a condensation product of 4‐aminopyrrole derivatives and dicyclohexylcarbodiimide
Authors: Bialer Meir , Yagen Boris , Mechoulam Raphael 
Published: March 2009

AbstractThe chemical structure of the two condensation products of dicyclohexylcarbodiimide (DCC) with the precursors of the mono‐pyrrole homologues of distamycin and with the mono and tri‐pyrrole homologues of congocidine were established. The two products isolated were proven to be condensation products between 4‐aminopyrrole derivatives and dicyclohexylcarbodiimide (DCC).
Chemical and biological modification of bleomycin, an antitumor antibiotic
Authors: Takita Tomohisa , Maeda Kenji 
Published: March 2009

AbstractDedicated to Professor John C. Sheehan on the occasion of his sixty‐fifth birthday.Chemical and biological modifications of bleomycin, an antitumor glycopeptide antibiotic, have been achieved by three procedures analogous to the modifications of penicillin.
Total synthesis of actinomycin D(C1) via a ring‐opening reaction of aziridine
Authors: Okawa K. , Nakajima K. , Tanaka T. 
Published: March 2009

AbstractActinomycin D(C1) has been synthesized by a route involving the ester formation between two peptide fragments, (2S,3S)‐1‐(2‐nitro‐3‐benzyloxy‐4‐methylbenzoyl)‐3‐methyl‐2‐aziridine‐carbonyl‐D‐valylproline t‐butyl ester and N‐benzyloxycarbonylsarcosyl‐N‐methylvaline, via a ring‐opening reaction of aziridine. Cyclization, followed by reduction and oxidation, gave actinomycin D(C1). The synthetic actinomycin D(C1) was indistinguishable from natural substance with respect to physical properties and biological activity.
Recent discoveries in the search for non‐opiate analgetics
Authors: Johnson M. Ross , Milne George M. 
Published: March 2009

AbstractA novel phenanthridine, nantradol (1), resulted from a search to dissect out analgetic activity from the cannabinoid molecule. Nantradol possesses two to seven times greater potency than morphine across a battery of analgetic tests. Despite this morphine‐like profile, nantradol does not bind to the opiate receptor. Nantradol has a total of five asymmetric centers and was studied as a 50:50 mixture of two diastereomers, both of which possess thetrans6a, 10a stereochemistry and have β‐oriented substituents at positions 6 and 9. Evidence is provided that, in common with the opiates, the analgetic actions of nantradol are stereospecific, the majority of the activity residing in a single levorotatory isomer. The stereospecificity and potency of the analetic effects of the nantradol series suggests a highly specific interaction at an as yet unidentified receptor.
Hetarylpyrazoles. II. Reactions of pyrazol‐l'‐ylpyridines
Authors: Khan Misbahul Ain , Pinto Alvaro Augusto Alves 
Published: March 2009

AbstractPyrazol‐l'‐ylpyridines undergo electrophilic substitution reactions (bromination, chlorination, and nitration) preferentially in the pyrazole ring. There is some evidence of the mutual influence of the pyrazole and the pyridine ring on the reactivity of the system. Some modifications of the substituents were also carried out. A dihydro derivative of a new ring system, pyrazolo[1′,2′‐a]pyrido[2,1‐c][l,2,4]triazine was also obtained.
The crystal structure of a trisisoxazole compound: 3‐(3‐Methyl‐5‐isoxazolyl)methyl‐5‐(3‐methyl‐5‐isoxazolyl)methylisoxazole
Authors: Albinati A. , Brückner S. , Malpezzi L. , Meille S. V. 
Published: March 2009

AbstractThe crystal structure of a trisisoxazole derivative is described. The crystals are monoclinic, space group P21/c (Z = 4) with cell dimensions: a = 8.846(4), b = 26.688(7), c = 9.081(4) Ä, β = 142.82(7)0. The structure was refined by full matrix least squares to a final R of 0.060. The molecule is non‐planar and the bond lengths and angles are in the expected range for isoxazole derivatives.
Transformations in the dibenzo[a,d]cycloheptene series
Authors: Coppola Gary M. , Hardtmann Goetz E. , Koletar Gabor , Kroin Stanley 
Published: March 2009

AbstractThe synthesis of 5‐aminomethyl‐5‐hydroxy‐5H‐dibenzo[a,d]cycloheptene derivatives 3 was accomplished by two separate routes. The first route involves the reaction of 4 with Corey's Reagent followed by reaction with either amines or hydrazines. The reaction products with hydrazines (e.g. 6) were hydrogenolyzed, either with hydrogen in the presence of platinum, or with hydrazine in the presence of Raney nickel to yield 3. The second route to these compounds (3) proceeds by a Reformatsky reaction on 4 followed by acid‐hydrazide formation and Curtius degradation of 8 to afford spirooxazolidones 9. Compounds 9 can be alkylated on nitrogen (10), and either 9 or 10 hydrolyzed to give the target compounds 3.
Studies in the synthesis and interconversion of isomeric triazolothienopyrimidines
Authors: Shishoo C. J. , Devani M. B. , Ullas G. V. , Ananthan S. , Bhadti V. S. 
Published: March 2009

Abstract4‐Hydrazinothieno[2,3‐d]pyrimidines were cyclized with triethyl orthoformate and formic acid to give 1,2,4‐triazolo[4,3‐c]thieno[3,2‐e]pyrimidines and 1,2,4‐triazolo[2,3‐c]thieno[3,2‐e]pyrimidines depending on the reaction conditions employed.
A reinvestigation of the stevens rearrangement of 1‐benzyl‐1,3,4‐trimethyl‐1,2,5,6‐tetrahydropyridinium salts
Authors: Bosch Joan , Rubiralta Mario , Domingo Antonio , Sistaré José 
Published: March 2009

AbstractAuthentic samples of 1,3,3‐trimethyl‐2‐(3,4,5‐trimethoxyphenyl)‐4‐methylenepiperidine (Ia) and 2‐(p‐chlorophenyl)‐1,3,3‐trimethyl‐4‐methylenepiperidine (Ib) are prepared by Mannich condensation between 4‐methyl‐1‐methylamino‐3‐pentanone hydrochloride (VI) and an aromatic aldehyde, followed by a Wittig reaction on the resulting 4‐piperidone. Comparing the physical and spectroscopic properties of Ia and Ib with those of the methylene derivatives IIa and IIb obtained as by‐products in the Stevens rearrangement of 1‐benzyl‐1,3,4‐trimethyl‐1,2,5,6‐tetrahydropyridinium salts IIIa and IIIb, respectively, it is shown that the assignment previously made for IIa and IIb is incorrect. Spectroscopic analysis (ir, 1H nmr, 13C nmr, ms) of these compounds and of its hydrogenation products VIII allows the structural and stereochemical assignment of 11a as cis‐3‐isopropenyl‐1,3‐dimethyl‐2‐(3,4,5‐trimethoxyphenyl)pyrrolidine and of IIb as cis‐2‐(p‐chlorophenyl)‐3‐isopropenyl‐1,3‐dimethylpyrrolidine. The formation of these rearrangement products is mechanistically interpreted as a Stevens [3,2] type process.
New synthesis of 7‐bromo‐1, 3‐dihydro‐3‐hydroxy‐5‐(2′‐pyridyl)‐2H‐1,4‐benzodiazepin‐2‐one
Authors: Kovač Tomislav , Belin Branka , Fajdiga Tatjana , Šunjić Vitomir 
Published: March 2009

AbstractA new synthesis of 7‐bromo‐1,3‐dihydro‐3‐hydroxy‐5‐(2′‐pyridyl)‐2H‐1,4‐benzodiazepin‐2‐one (5) is described. Starting from bromazepam (3), C(3) acylation with lead tetraacetate/potassium iodide in acetic acid affords4, while its mild hydrolysis according to our recently described method (5) gives5. Improved hexamine cyclization of1into3,viaquaternary hexaminium salt2, is discussed, and identification of the intermediates7and8is performed. Compound5undergoes on melting, or on brief heating in glacial acetic acid, the thermal rearrangement into quinazolin‐2‐aldehyde (13), the structure of which is confirmed by oxidation into the ester14, which in turn was hydrolyzed to the acid15. The same compound (5) rearranges on heating with manganese(III) acetate in acetic acid into the 3‐amino‐2‐quinolone derivative6. On heating in glacial acetic acid in the presence of lead tetraacetate/potassium iodide (or iodine), compound4, in addition to giving the aldehyde13, ester14and acid15rearrangement products, affords 1,2‐dihydroquinazolin‐2‐carboxylic acid16.
Reissert compound studies. XXXIX. A novel approach to the berbine and 6‐azaberbine systems and related derivatives of ellipticine
Authors: Veeraraghavan Seshadri , Popp Frank D. 
Published: March 2009

AbstractA new synthetic method for the construction of the berbine, 6‐azaberbine, and indoloberbine ring skeletons is reported. Treatment of heterocyclic bases such as isoquinolines, phthalazines, and ellipticine with 2‐chloromethylbenzoyl chloride and trimethylsilyl cyanide gave the corresponding Reissert compounds. Treatment of these Reissert compounds with sodium hydride resulted in intramolecular cyclization with loss of hydrogen cyanide.
Fused s‐triazino heterocycles. VIII. 1,3,4,6,9b‐pentaazaphenalenes. Reactions of a methyl and bromomethyl side chain
Authors: Shaw John T. , Brotherton Christine E. , Moon Robert W. , Coffindaffer Timothy W. , Miller Deborah A. 
Published: March 2009

AbstractEnhanced reactivity of the methyl group of 2‐t‐butyl‐5‐methyl‐1,3,4,6,9b‐pentaazaphenalene allowed acetic anhydride‐catalyzed condensation reactions with several aromatic aldehydes, and base‐catalyzed alkylation reactions with several alkyl halides to take place, albeit in low yields. Of the many nucleophiles tried, only salts of carboxylic acids, in the presence of 18‐crown‐6, were able to displace bromine from 2‐(bromomethyl)‐5‐methyl‐1,3,4,6,9b‐pentaazaphenalene.
Derivatives of 2,3,8,9‐tetrahydro‐3‐oxo‐1H‐benz[de]isoquinoline‐1,9a‐(7H)dicarboximide
Authors: Campaigne E. , Yodice Richard 
Published: March 2009

AbstractThe synthesis of a series of derivatives of 2,3,8,9‐tetrahydro‐3‐oxo‐1H‐benz[de]isoquinoline‐1,9a‐(7H)dicarboximide (1) are described. Alkylations and thionations of 1 produced a variety of interesting heterocycles. In addition, triazole and triazolone rings were fused to 1 to produce novel compounds. These structures were of interest as potential anticonvulsants.
Synthesis of 1‐alkyl and 1,3‐dialkyl‐2‐benzimidazolones from 1‐alkenyl‐2‐benzimidazolones using phase‐transfer catalysis technique
Authors: Vernin Gaston , Domlog Hicham , Siv Chan , Metzger Jacques , El‐Shafei Ahmed Kamal 
Published: March 2009

AbstractA general synthetic route to 1‐alkyl and 1,3‐dialkyl‐2‐benzimidazolones from 1‐alkenyl‐2‐benzimidazolones using phase‐transfer catalysis conditions is described.