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1.
Maria Rosaria Del Giudice Franco Gatta Guido Settimj 《Journal of heterocyclic chemistry》1990,27(4):967-973
Oxidation of 1-methyl-3-methoxycarbonyl-β-carboline with selenium dioxide gave 1-formyl-3-methoxycarbonyl-β-carboline II . Compound II reacted with acetic or propionic anhydride to give easily the 2-methoxycarbonyl-6H-indolo[3,2,1-d,e][1,5]naphthyridin-6-ones III ; reaction of II with some primary amines led to the formation of the Schiff bases IV , which were reduced to the 1-aminomethyl-3-methoxycarbonyl-β-carbolines V with sodium borohydride. Cyclization of V with aqueous formaldehyde led to the pyrimido[3,4,5-lm]pyrido[3,4-b]indoles VI . Analogously, cyclization with formaldehyde, acetone or 1,1′-carbonyldiimidazole of the 3-aminomethyl- 1,2,3,4-tetrahydro-β-carbolines VIII , obtained by reaction of 3-methoxycarbonyl-1,2,3,4-tetrahydro-β-carboline VII with amines followed by lithium aluminium hydride reduction of the resulting amides, gave the imidazo[1′,5′-1,6]pyrido[3,4-b]indoles IX and X . Dieckmann cyclization of 3-methoxycarbonyl-2-[(3-ethoxycarbonyl)-1-propyl]-1,2,3,4-tetrahydro-β-carboline XI led to a 1:1 mixture of the β-ketoesters XII and XIII , which underwent deethoxycarbonylation to 5,6,8,9,10,11,11a,12-octahydroindolo[3,2-b]quinolizin-11-one XIV . Finally, the polyphosphoric acid (or esters) catalyzed cyclization of the N-acyl derivatives XVI of 3-hydrazinocarbonyl-β-carboline XV led smoothly to the 3-(1,3,4-oxadiazol-2-yl)-β-carbolines XVII . 相似文献
2.
《Tetrahedron: Asymmetry》2001,12(7):975-978
Sulfoxidation of the (+)-Noe-lactol derivative of racemic 6,11-dihydrodibenzo[b,e]thiepin-11-ol broke the isosterism and converted an inseparable mixture of two compounds into a separable mixture of four. X-Ray structural determination on one of these and subsequent manipulation provided resolved 6,11-dihydrodibenzo[b,e]thiepin-11-ol and all four sulfoxides in known configurations, and enabled the resolution by synthesis of the two isosteric diastereoisomers of the calcium channel blocker UK-74,756. 相似文献
3.
The 1,3-dipolar addition of acetylenedicarboxylic esters (IX and X) to 2-methyl-4-phenyl-quinazoline 3-oxide (VIII) in benzene/methanol and benzene/ethanol, respectively, gives the esters XI and XII of 3-amino-3-phenyl-2-(2-acetamidophenyl)-acrylic acid as main products and the esters XIII and XIV of 2-methyl-4-phenyl-5H-benzo[d][1,3]diazepin-5-carboxylic acid as by-products. The constitutions of XI and XII are elucidated by acid hydrolysis to the 2-phenylindole-3-carboxylic esters VI and VII, respectively, and by ozonolysis of XII to give benzamide and ethyl o-acetamido-mandelate (IV). The alkaline hydrolysis of XI or XII gives the enamine derivative XVIII, which is hydrolysed by acid to oxindole and benzoic acid. The structure elucidation of XIII and XIV is based on spectroscopic data together with thc formation of XV by alkaline hydrolysis. Mechanisms arc proposed for the reaction paths. 相似文献
4.
Treatment of 4-[(3-hydroxy-2-pyridyl)amino]-2-phenyl-5-pyrimidinecarboxylic acid (X) with acetic anhydride under refluxing conditions afforded 10-hydroxy-2-phenyl-5H-pyrido[1,2-a]-pyrimido[4,5-d]pyrimidin-5-one acetate (IX). The intermediate X was prepared from 4-chloro-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester (V). The reaction of V with the sodium salt of 2-amino-3-hydroxypyridine at room temperature gave 4-(2-amino-3-pyridyloxy)-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester (VI). Treatment of VI with a hot aqueous sodium hydroxide solution and subsequent acidification gave X. Involvement of 4-[(3-hydroxy-2-pyridyl)amino]-2-phenyl-5-pyrimidinecaroboxylic acid ethyl ester (VIII) (Smiles rearrangement product) as an intermediate in the above alkaline hydrolysis reaction of VI to X was demonstrated by the isolation of VIII and its subsequent conversion into X under alkaline hydrolysis conditions. Acetylation of VIII with acetic anhydride in pyridine solution gave 4-[(3-hydroxy-2-pyridyl)amino]-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester acetate (XI), which afforded IX on fusion at 220°. This alternative synthesis of IX from XI supported the structural assignment of IX. Fusion of VI gave 10-hydroxy-2-phenyl-5H-pyrido[1,2-a]pyrimido]4,5-d]pyrimidin-5-one (VII). The latter was also obtained when VIII was fused at 210°. Acetylation of VII with acetic anhydride afforded IX. 相似文献
5.
J. O. Jílek V. Seidlová E. Svátek M. Protiva 《Monatshefte für Chemie / Chemical Monthly》1965,96(1):182-207
Zusammenfassung Im Rahmen der Suche nach neuen neurotropen und psychotropen Substanzen, besonders nach antidepressiv wirkenden Psychopharmaka, wurde eine systematische präparative Arbeit in den Gruppen der 10-substituierten Derivate des 10,11-Dihydrodibenzo[a,d]cycloheptens (I) und des 10,11-Dihydrodibenzo[b,f]-thiepins (II) unternommen. Im ersten Fall war die Ausgangssubstanz das Keton XIV, das mit üblichen Methoden zum basischen Äther XVI, zu Aminen und Derivaten XVIII–XXII und schließlich in dieMannich-Base XXVI übergeführt wurde. DieBeckmannsche Umlagerung des Oxims XVII eröffnete den Weg zu Derivaten eines neuen Systems, des 5,6,7,12-Tetrahydrodibenz[b,e]azocins (Verbindungen XXVIII, XXX und XXXI). Auch im zweiten Fall bildete das entsprechende Keton (XXXVIII) die Schlüsselsubstanz, die einerseits zu Aminen mit der Aminogruppe in der Seitenkette (XXXIX, XL, XLII, LV, LVI), anderseits zu Aminen mit der direkt am Skelett haftenden Aminogruppe (XLIV–LIII) umgesetzt wurde. Außer den angeführten Aminen wurde in allen drei Gruppen eine Reihe von neutralen Verbindungen hergestellt (Zwischenprodukte und Nebenprodukte), deren Struktur meistens mit Hilfe der Spektren geklärt wurde. Die vorläufigen Ergebnisse der pharmakologischen Prüfung einiger Produkte deuten interessante Wirksamkeit an, besonders vom Standpunkt der erwarteten neurotropen und psychotropen Eigenschaften aus.
mit technischer Hilfe von
Herrn Professor Dr.Hermann Bretschneider zum 60. Geburtstag gewidmet
4. Mitt.:J. O. Jílek, K. Pelz, D. Pavlíková undM. Protiva, Coll. Czechoslov. Chem. Commun.30, im Druck (1965). 相似文献
In the effort to find new neurotropic and psychotropic substances a systematic chemical study was undertaken in the groups of the 10-substituted derivatives of 10,11-dihydrodibenzo[a,d]-cycloheptene (I) and 10,11-dihydrodibenzo[b,f]thiepine (II). In the first case the ketone XIV was transformed by usual methods into the basic ether XVI, to the amines and derivatives XVIII–XXII, and to theMannich base XXVI. TheBeckmann rearrangement of the oxime XVII opened the way to derivatives of a new system — 5,6,7,12-tetrahydrodibenz[b,e]azocine (compounds XXVIII, XXX and XXXI). In the second case (derivatives of II) the syntheses started from the ketone XXXVIII and two series of amines were prepared: with the amino group in the side chain (XXXIX, XL, XLII, LV, LVI) and with the amino group attached directly to the skeleton (XLIV–LIII). In addition to the amines several neutral compounds in either group were synthesized (intermediates and byproducts), the structure of which was elucidated mainly by means of the spectra. Preliminary results of the pharmacological testing show a rather important degree of activity of some substances, especially in the line of the expected neurotropic and psychotropic properties.
mit technischer Hilfe von
Herrn Professor Dr.Hermann Bretschneider zum 60. Geburtstag gewidmet
4. Mitt.:J. O. Jílek, K. Pelz, D. Pavlíková undM. Protiva, Coll. Czechoslov. Chem. Commun.30, im Druck (1965). 相似文献
6.
Dijana Pei Ivana Ozimec Landek Renata Rup
i Marina Modri Iva Dapo Rudolf Trojko Mladen Merep Milan Mesi 《Journal of heterocyclic chemistry》2012,49(2):243-252
The present review focuses on dibenzo[b,f]oxepin‐10(11H)‐one ( I , X = O) and dibenzo[b,f]thiepin‐10(11H)‐one ( I , X = S) as common synthons in the efficient synthesis of various dibenzoxepino[4,5‐ and dibenzothiepino[4,5]‐fused five‐membered heterocycles: [2,3] fused thiophene ( II ), [3,4] fused thiophene ( III ), furan ( IV ), pyrrole ( V ), imidazole ( VI ), pyrazole ( VII ), oxazole ( VIII ), and thiazole ( IX ). The potential of I to be converted into reactive intermediates that readily undergo heteroaromatic annulation reactions by cyclocondensation with proper binucleophiles allows formation of a range of enumerated functionalized dibenzo[e,h]azulene [4] structures ( II , III , IV , V , VI , VII , VIII , IX ). Dibenzo[e,h]azulenes as heterotetracyclic scaffold can be exploited in further modifications to obtain compounds with altered physicochemical and biological profile. J. Heterocyclic Chem., (2012). 相似文献
7.
The nitro-imidazolines V and VI are formed by addition reaction of ethylenediamine to the isothiocyanates III and IV. The nitro group is then converted by hydrogenation to the amino group, giving XI and XII, which can be acylated selectively to IX and X. By rearrangement in boiling xylene, the compounds XI and XII give the corresponding 2-(2-aminoethylamino)-benzimidazoles XIII and XIV. The benzoylated derivative IX gives the benzimidazole derivative XVIII by rearrangement and subsequent migration of the benzoyl group, while the benzylated derivative XVI gives the rearranged benzimidazole XXII. The benzimidazole structure of the rearranged products is proven by unambiguous synthesis of XIII, starting with 2-chlorobenzimidazole (VII) and mono-N-acetyl-ethylene-diamine to give compound VIII, from which XIII is obtained by hydrolysis. 相似文献
8.
Sadao Nishigaki Misuzu Ichiba Kiyoko Fukami Keitaro Senga 《Journal of heterocyclic chemistry》1982,19(4):769-773
Reaction of 5-arylazo-6-arylidenehydrazino-1,3-dimethyluracils (II), prepared by the treatment of 6-aryl-idenehydrazino-1,3-dimethyluracils (I) with diazotized arylamines, with dimethylformamide dimethylacetal resulted in the formation of pyrimido[5,4-e]-as-triazine (V) system, while the thermolysis of II resulted in the formation of purine (X), v-triazolo[4,5-d]pyrimidine (XII), and pyrazolo[3,4-d]pyrimidine (XIV, XIX) systems in lieu of the expected V. Reasonable mechanisms have been proposed for the formation of the various ring systems in these reactions. 相似文献
9.
The condensation of 4-amino-2,1,3-benzothiadiazole (IV) with diphenyliodonium-2-earboxylate gave N-(2,1,3-benzothiadiazoI-4-yl)anthranilic acid (V) (28%), which was cyclized with phosphorus oxychloride to 6-chloro[1,2,5]thiadiazolo[3,4-c]acridine (VI) (84%). Treatment of VI with 3-(dimethylamino)-1-propanethiol hydrochloride in phenol afforded 6-[ [3-(dimethylamino)-propyl]thio] [1,2,5]thiadiazolo[3,4-c]acridine (VII) (65%). The reaction of IV with a mixture of methyl and ethyl 2-oxocyclohexanecarboxylate gave the adduct, which was ring closed in Dowtherm to 7,9,10,1 1-tetrahydro[1,2,5] thiadiazolo[3,4-c]acridin-6(8H)one (VIII) (70%). Chlorination of VIII with phosphorus oxychloride gave 6-chloro-7,8,9,10-tetrahydro[1,2,5]thiadiazolo[3,4-c]acridine (IX) (84%), which was condensed with 3-(dimethylamino)-1-propanethiol hydrochloride in phenol yielding 6-[ [3-(dimethylamino)propyl]thio]-7,8,9,10-tetrahydrof 1,2,5]-thiadiazolo[3,4-c]acridine (X) (27%). 6-[ [3(1)imethylamino)propyl]thio]-8,9-dihydro-7H-cyclopenta[b] [1,2,5]thiadiazolo[3,4-h]quinoline (XIII) (25%) was prepared similarly from IV and a mixture of methyl and ethyl 2-oxocyclopentanecarboxylate via 7,8,9,10-tetrahydro-6H-cyclopenta[b][1,2,5]thiadiazolo[3,4-h]quinolin-6-one (XI) (85%) and 6-chloro-8,9-dihydro-7H-cyclopenta[b][1,2,5]thiadiazolof3,4-h]quinoline (XII) (56%). The effects of compounds VII-XIII as inhibitors of platelet aggregation are discussed. 相似文献
10.
2-Amino-6-bromomethyl-5-phenylbutyl-4-pyrimidinol (IV) smoothly alkylated triphenyl phosphine, resulting in a 95% yield of the phosphonium salt (V). This Wittig reagent (V) readily condensed with p-nitrobenzaldehyde, p-nitrocinnamaldehyde, or cinnamalde-hyde in N,N-dimethylformamide to give the 6-(p-nitrostyryl) (X), 6-(p-nitrophenyl-1,3-butadien-1-yl) (VIH), and 6-(phenyl-1,3-butadien-1-yl) (IX) pyrimidinols in 72, 67 and 44% yields, respectively. Catalytic reduction of VIII and IX afforded the corresponding 6-(p-aminophenylethyl) (XII) and 6-(p-aminophenylbutyl) (XI) 4-pyrimidinols. 相似文献
11.
The reaction of thioxanthylium perchlorate with diazomethane was investigated. Depending on the reaction conditions, seven compounds (II, III, V, VI, VIII, IX, and X) are formed which were identified on the basis of spectral data (mainly mass spectra) and chemical reactions. A synthesis was worked out (reaction of compound VII with boron trifluoride) in which dibenzo[b,f]thiepine (VIII) is formed as major product (55%). 相似文献
12.
Maruti H. Sonar A. Sitaramachandra Murty 《Monatshefte für Chemie / Chemical Monthly》1977,108(5):1243-1252
The complexes of cobalt(II) chloride with o, m, p-tolyl thiourea (I–III); m, p-nitrophenyl thiourea (IV, V); o, m, p-hydroxy phenyl thiourea (VI–VIII); m, p-bromophenyl thiourea (IX, X); p-iodophenyl thiourea (XI) and o-bromo-p-methyl phenyl thiourea (XII) have been synthesised. The elemental analysis reveals that ligands (I–V) form bis and the rest forms tris complexes with cobalt(II). Infrared and farinfrared spectral measurements prove that sulphur is taking part in co-ordination. All complexes are nonelectrolytes in acetone as revealed by conductivity measurements. The data obtained from magnetic susceptibility measurements, electronic spectra in solution are consistant with a practically tetrahedral symmetry. 相似文献
13.
Hamdy A. Hammouda Ahmed A. El-Barbary Mohie A. F. Sharaf 《Journal of heterocyclic chemistry》1984,21(4):945-947
5-Amino-3-phenylpyrazole (I) and 5-amino-4-bromo-3-phenylpyrazole (II) reacted with ethyl acetoacetate and acetylacetone to give various pyrazolo[1,5-a]pyrimidines IV-VI and with benzoins to give different fused pyrazoles, namely, imidazo[1,2-b]pyrazoles IX, pyrrolo[2,3-c]pyrazoles X and pyrazolo[4,3-b][1,4]oxazines XII. Diazotized II was coupled with active methylene-containing nitriles to afford pyrazolo[5,1-c]-as-triazines XIV. 相似文献
14.
Several pyridazines have been prepared as intermediates in the synthesis of monosubstituted imidazo[4,5-d]pyridazines, monosubstituted v-triazoIo[4,5-d]pyridazines and monosubstituted pyrazino [2,3d] pyridazines. The new ring system, 7H-imidazo[4,5-d]tetrazolo[l,5-b] pyridazine (XIV) has been prepared unsubstituted. Furthermore, unsubstituted imidazo[4,5-d]pyridazine (XI) has been prepared. Calculations for XI and XIV were made by approximate SCF LCAO-MO with CNSO II theory. 相似文献
15.
Jerald S. Bradshaw John E. Tueller Steven L. Baxter Garren E. Maas John T. Carlock 《Journal of heterocyclic chemistry》1977,14(3):411-414
s-Triazolo[4,3-b]pyridazine (I) reacted photochemieally with bieyélo[2.2.1] hepla-2,5-diene, 1,5-cyclooctadiene, 1,3-cyclooctadiene, methylene cyclohexane, diethyl cis-1,2,3,6-tetrahydro-phthalate and ethyl 2-cyclopentene-1-acetate to givt: the following products: the endo and exo isomers of 4a, 5, 8a, 9-tetrahydro-9-rnethylene-5,8-rnethano-8H-s-triuzolo[1, 5-a]indole (II) and the endo and exo-9-cyanometliyl products (III and IV) from bicyclo[2.2.1] hepta-2,5-diene; 4a,5,-9, 10, 10a, 11-huxahydro-11-methylene-6H-cycloocta[4,5]pyrrolo[1,2-b]-s-triazole (V) and the 11-cyanomethyl product VI from 1,5-cyclooctadiene: 4a,7,8,9,10,10a-hexahydro-11 -inethylene-11H-cycloocta[4,5]pyrrolo[1,2-b]-s-triazole(VII),4a, 5, 7, 8, 10a, 11-hexahydro-11-methylene-6H-cycloocta[4,5]pyrroIo[1,2-b]-s-triazole (VIII) and their respective 9-cyanomethyl products (X and 1X) from 1,3-cyclooctadiene; 6′, 7′ -dihydro-7′ -methylenespiro[cyclohexane-1, 5′-[5H] pyr-rolo[1,2-b]-s-triazole] (XI), 6′, 7′-dihydro-7′-meth) lene. spiro cyclohexane-1, 6′-[5H]pyrrolo[1,2-b]-s-triazole] (XII) and their respective 7 -eyanomethyl products (XIII and XIV) from melhylene cyclohexane; 6,7-dicarbethoxy-9-cyanomelhyl-4a, 5, 7, 8, 8a, 9-hexahydro-6H-s-triazolo[1,5-a]indole (XV) from diethyl cis-1, 2, 3, 6-tetrahydrophlhalate: and 5-earl)elhoxymethyl-8-eyanomethyl-4a, 5, 6, 7, 7a, 8-hexahydrocyclopenta[4,5]pyrrolo( 1, 2-b]-s-triazole (XVI) from ethyl 2, 2-cyclo-pentene-1-acetate. Many other alkenes, particularly the phenyl ethylenes, did not react with compound 1. In general, more than one product was isolated for each reaction except in the case of the two ester alkenes where a single eyanomethyl product was observed. 相似文献
16.
Edward F. Elslager Jane Clarke Judith Johnson Leslie M. Werbel John Davoll 《Journal of heterocyclic chemistry》1972,9(4):759-773
2 Various4-diamino-6-(phenoxy, naphthyloxy, and phenalkoxy)quinazolines (VIII, XIV) were synthesized for antimalarial and antibacterial evaluation. Treatment of the anion of the requisite phenol or naphthol with 5-chloro-2-nitrobenzonitrile (V) gave the corresponding 2-nitro-5-(phenoxy and naphthyloxy)benzonitriles (VI) (33–78%). Alternatively, alkylation of 5-hydroxy-2-nitrobenzaldehyde (IX) with the appropriate phenalkyl halide afforded the 2-nitro-5-(phenalkoxy)benzaldehydes (X) (27–62%), which were converted to the 2-nitro-5-(phenalkoxy)benzonitriles (XII) via the intermediate oximes XI (62–87% overall). Reduction of the 2-nitrobenzonitriles (VI, XII) with stannous chloride-hydrochloric acid provided the corresponding 2-amino-5-(phenoxy, naphthyloxy, and phenalkoxy)benzonitriles (VII, XIII) (30–83%), which upon cyclization with chloroformamidine hydrochloride gave the 2,4-diaminoquinazolines VIII and XIV (12–85%). Against Plasmodium berghei in mice, eleven compounds were active orally at doses ranging from 6.3 to 174 mg./kg./day for 6 days, while seven substances displayed activity subcutaneously following single doses of 40–640 mg./kg. Fifteen compounds exhibited in vitro antibacterial activity against Streptococcus faecalis (MGH-2), normal (UC-76) and drug-resistant (S18713) Staphylococcus aureus, Escherichia coli (Vogel), and Shigella sonnei (C-10) with MIC's ranging from < 0.25 to 20 μg./ml. (gradient plate). Data on the inhibitory effects of representative compounds against Streptococcus faecalis R (S. faecium var. durans), S. faecalis A (amino-pterin, methotrexate-resistant), and Lactobacillus plantarum are presented, and overall structure-activity relationships are discussed. 相似文献
17.
Stereospecifity of the neuroleptic activity and chirality of (+)-3-{2-[4-(8-fluoro-2-methyl-10, 11-dihydrodibenzo[b,f]thiepin-10-yl)-1-piperazinyl]ethyl}-2-oxazolidinone (16). The synthesis and stereospecific neuroleptic action in animals of the (+)-enantiomer of 3-{2-[4-(8-fluoro-2-methyl-10,11-dihydrodibenzo [b,f]thiepin-10-yl)-1-piperazinyl]ethyl}-2-oxazolidinone ( 16 ) are briefly described. The (10S)-configuration of this compound was determined by X-ray diffraction. 相似文献
18.
A series of 3-substituted octahydroimidazo[1,5-a]pyridines has been prepared. An nmr study at several temperatures showed that 3-phenyloctahydroimidazo[1,5-a] pyridine (XIII) and 3-t-butyloctahydroimidazo[1,5-a] pyridine (XIV) exhibited ring-chain tautomerism. The n-propyl (X), isopropyl (XI) and benzyl (XII) derivatives did not show this form of isomerism. It has also been shown that Crabb and Newton's statement (3) that Freed and Day (1) had failed to obtain the parent compound, octahydroimidazo[1,5-a]pyridine (1), is incorrect. 相似文献
19.
Ulrich Wannagat Farroch Rabet Hans-Jürgen Wismar 《Monatshefte für Chemie / Chemical Monthly》1971,102(5):1429-1441
Zusammenfassung Die achtgliedrigen Ringverbindungen IX (Rk. 1), XI (Rk. 12), XI (RRk. 13) und XIV (Rk. 9a) (vgl. Schema 1) wurden erstmalig, XII (Rkk. 4, 8; Schema 2) auf neuen Wegen dargestellt, ihre Eigenschaften beschrieben und ihre Struktur durch Massen-, IR-und NMR-Spektren bestätigt. Sie neigen bei thermischem deer katalytischem Einfluß zum Übergang in sechsgliedrige Ringverbindungen (vgl. Schema 3).
Herrn Prof. Dr. Dr. h. c.H. Nowotny gewidmet.
103. Mitt.:U. Wannagat undL. Gerschler, Z. anorg. allgem. Chem. (im Druck).
Mit Auszügen aus den Dissertationen a)F. Rabet und b)H. J. Wismar, Techn. Universität Braunschweig, 1971. 相似文献
N-Methylated cyclotetrasilazanes and cyclotetrasiloxazanes (chemistry of silicon-nitrogen compounds, CIV)
The eightmembered ring compounds IX (equ. 1), XI (equ. 12), XII (equ. 13) and XIV (equ. 9a) (see scheme 1) were prepared for the first time, XII (equ. 4, 8; scheme 2) on several new routes. Their properties are described and their structure confirmed by mass, infrared and nmr spectroscopy. They tend to transform by thermal or catalytic influence into sixmembered ring compounds (compare scheme 3).
Herrn Prof. Dr. Dr. h. c.H. Nowotny gewidmet.
103. Mitt.:U. Wannagat undL. Gerschler, Z. anorg. allgem. Chem. (im Druck).
Mit Auszügen aus den Dissertationen a)F. Rabet und b)H. J. Wismar, Techn. Universität Braunschweig, 1971. 相似文献
20.
Norman L. Colbry Edward F. Elslager Leslie M. Werbel 《Journal of heterocyclic chemistry》1984,21(5):1521-1525
The synthesis and antimalarial activity of a series of 2,4-diamino-6-[(aryl)thio, sulfinyl and sulfonyl]pyrido-[3,2-d]pyrimidines is described. Nitration of 2,6-dichloropyridine provided the 3-nitro derivative which was converted to 6-chloro-3-nitro-2-pyridinecarbonitrile (V) with cuprous cyanide. Condensation of an aryl thiol with V gave the 6-arylthiopyridines VI which were reduced with iron in hydrochloric acid and condensed with chloroformamidine to give the 6-arylthiopyrido[3,2-d]pyrimidin-2,4-diamines X. Alternatively V was reduced to the amine VIII condensed with chloroformamidine and the resulting 6-chloropyrido[3,2-d]pyrimidine (IX) was treated with an arylthiol. Oxidation of X provided sulfinyl and sulfonyl analogs. 相似文献