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Showing papers on "Benzopyran published in 1984"


Journal ArticleDOI
TL;DR: In this paper, short syntheses of the extremely potent benzopyran prostacyclin mimics 26 and 27 were described using a novel intramolecular Mitsunobu reaction (e.g. 20 → 22) in the key step.

32 citations


Journal ArticleDOI
TL;DR: Synthese du compose du titre et de l'analogue phenylthiomethyl-7 a partir de la condensation de la khellinone avec les methylthio-and phenyl-thioacetates d'ethyle as discussed by the authors.
Abstract: Synthese du compose du titre et de l'analogue phenylthiomethyl-7 a partir de la condensation de la khellinone avec les methylthio- et phenylthioacetates d'ethyle. Transpositions, desulfuration, oxydation, reduction

21 citations


Patent
06 Nov 1984
TL;DR: In this paper, the authors describe the manufacture of (oxo-4-4H-(1)-benzopyran-8-yl) alkanoic acids and their derivatives, represented by the formula: ##STR1## where Ar is hydrogen, a phenyl radical which may or may not be substituted, thenyl, furyl, naphthyl, a lower alkyl, cyclo-alkyl, aralkyl radical, B is a linear or branched lower-alkyl radical, either saturated or ethylinically
Abstract: The invention concerns: (oxo-4-4H-(1)-benzopyran-8-yl) alkanoic acids and their derivatives, their manufacture, represented by the formula: ##STR1## where Ar is hydrogen, a phenyl radical which may or may not be substituted, thenyl, furyl, naphthyl, a lower alkyl, cycloalkyl, aralkyl radical; B is a linear or branched lower alkyl radical, either saturated or ethylinically unsaturated; R1 is hydrogen or a phenyl radical; X is hydrogen or a lower alkyl or alkoxy radical and n=1, as well as salts, esters, aminoesters and amides. Compounds and their derivatives may be used as medicines, in particular in the control of tumors.

17 citations


Journal ArticleDOI
TL;DR: A series of novel substituted trans-4-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ols was prepared and tested for antihypertensive activity in the conscious deoxycorticosterone acetate/saline treated hypertensive rat.
Abstract: A series of novel substituted trans-4-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ols was prepared and tested for antihypertensive activity in the conscious deoxycorticosterone acetate (DOCA)/saline treated hypertensive rat. Optimum blood pressure lowering activity requires 6-substitution by a strong electron-withdrawing group, together with a pyrrolidino or piperidino group at the 4 position. Exceptions to this were the 7-nitro-4-pyrrolidine analogue and the 6-nitro-3-chloropropylamine, which retained marked antihypertensive activity. All of these compounds were direct vasodilators and had comparable antihypertensive activity to hydralazine and to the calcium antagonist, nifedipine. The synthetic route to these compounds involves cyclization of of propargyl ethers to 2H-1-benzopyrans, followed by conversion via bromohydrins to 3,4-epoxides, which were ring opened with the appropriate amines. Meta-substituted propargyl ethers gave both 5- and 7-substituted benzopyrans on thermal cyclization, the former predominating. A new route to 2,2-dimethyl-7-nitrobenzopyran is described.

14 citations







Journal ArticleDOI
TL;DR: Les composes du titre sont obtenus par condensation d'hydroxy-4 coumarines avec l'isoprene suivie de deshydrogenation avec le DDQ; obtention egalement par cette condensation de dimethyl-2,2 tetrahydro-2.3,4,5 pyranno [2,3-b] benzopyranne-1ones-5 as mentioned in this paper.
Abstract: Les composes du titre sont obtenus par condensation d'hydroxy-4 coumarines avec l'isoprene suivie de deshydrogenation avec le DDQ; obtention egalement par cette condensation de dimethyl-2,2 tetrahydro-2,3,4,5 pyranno [2,3-b] benzopyranne-1ones-5

6 citations



Journal ArticleDOI
TL;DR: The authors derives hydroxymethyl-2 des composes du titre sont les produits principaux de la reaction du S,S-dimethyl sulfoxoniomethanure sur les adduits de Michael d'hydroxy-4 coumarines and d'enones.
Abstract: Les derives hydroxymethyl-2 des composes du titre sont les produits principaux de la reaction du S,S-dimethyl sulfoxoniomethanure sur les adduits de Michael d'hydroxy-4 coumarines et d'enones (dihydro-3,4 hydroxy-2 2,5H-pyranno [3,2-c] benzopyranne-1ones-5); obtention egalement de quantites mineures d'hydroxymethyl-2 tetrahydro-2,3,4,5 pyranno [2,3-b] benzopyranne-1ones-5



Journal ArticleDOI
G. E. Stokker1
TL;DR: The reaction of 4,6-dichloro-2-(methylthiomethoxy)cinnamaldehyde (3) with mercuric chloride in hot aqueous acetonitrile gave 5,7 dichloros 2H-1-benzyopyran-2-ol (4) in good yield as discussed by the authors.

Journal ArticleDOI
TL;DR: In this article, the hyperfine structure of the EPR spectra of 1,3,3-trimethyl-5-nitrospiro (indoline-2,2′-[2H]chromene) was analyzed and it was shown that cleavage of the spiro carbon atom and the oxygen atom in the pyran ring does not occur in the formation of the anion radical.
Abstract: Electrochemical generation was used to obtain anion radicals of 1,3,3-trimethyl-5-nitrospiro (indoline-2,2′-[2H]chromene), and their EPR spectra in acetonitrile, dimethylformamide (DMF), and dimethyl sulfoxide (DMSO) were recorded. On the basis of an analysis of the hyperfine structure (hfs) of the EPR spectra it was concluded that, as a consequence of the relatively weak interaction of the π-systems of the indoline and benzopyran fragments, cleavage of the bond between the spiro carbon atom and the oxygen atom in the pyran ring does not occur in the formation of the anion radical, and the additional unpaired electron is delocalized in the π-system of the indoline fragment of the molecule.

Patent
14 Feb 1984
TL;DR: In this paper, a compound (salt) shown by the formula I (one of X and Y is O, and the other is methylene or carbonyl; A is H, halogen, methyl, acetyl, cyanoethyl, etc.).
Abstract: NEW MATERIAL:A compound (salt) shown by the formula I (one of X and Y is O, and the other is methylene or carbonyl; A is H, halogen, methyl, acetyl, cyanoethyl, etc.; B is H, halogen, methyl, alpha-cyanoethyl, methoxycarbonylmethyl, etc.; C is H, halogen, methyl, methoxycarbonylmethyl, etc.; D and E are H, halogen, or methyl; with the proviso that the case wherein X is O, Y is carbonyl, and A-E are H is omitted). EXAMPLE:9H-Thieno[3,2-b][1] benzopyran-2-propionic acid. USE:An antiphlogistic. PROCESS:For example, a 3-alkoxythiophene is reacted with o-anisoyl chloride to give a compound shown by the formula II, which is subjected to ring closure to give 9H-thieno[3,2-b][1] benzopyran shown by the formula III, which is further acetylated, converted into a nitrile group, and hydrolyzed, to give a compound shown by the formula I .



Journal ArticleDOI
TL;DR: New penamic and cephemic derivatives that contain a 1-[2H]isoquinolinone or 1H-2-benzopyran-1-one ring in an acylaminoside chain were synthesized as mentioned in this paper.
Abstract: New penamic and cephemic derivatives that contain a 1-[2H]isoquinolinone or 1H-2-benzopyran-1-one ring in an acylaminoside chain were synthesized. It was established that compounds in the form of carboxylic acids or sodium salts display activity in vitro with respect to pathogenic microorganisms.

Journal ArticleDOI
TL;DR: In this article, condensation of 2-methylsulfinylmethyl-1, 3-dicarbonyl compounds (3) with 4-hydroxycoumarin (5) at ambient temperature gave 2.
Abstract: Michael condensation of 2-methylsulfinylmethyl-1, 3-dicarbonyl compounds (3) or 2-methylene-1, 3-dicarbonyl compounds (4) with 4-hydroxycoumarin (5) at ambient temperature gave 2-[(4-hydroxycoumarin-3-yl)methyl]-1, 3-dicarbonyl compounds (6). Treatment of 6 with methanolic hydrogen chloride resulted in the regioselective formation of 2, 2, 3-trisubstituted-3, 4-dihydro-2H-pyrano[3, 2-c][1]benzopyran-5-ones.