Showing papers on "Pyran published in 1970"
TL;DR: Pyran copolymer, administered with sheep red blood cells to mice, enhances the early rate of appearance of antibody-forming spleen cells, with major effect on macrophages.
Abstract: SummaryPyran copolymer, administered with sheep red blood cells to mice, enhances the early rate of appearance of antibody-forming spleen cells. Although the cytotoxicity and pyrogenicity of pyran and bacterial endotoxins are similar, pyran, in contrast to endotoxin, does not trigger a nonspecific initiation of antibody formation; it only enhances specific responses. The major effect of pyran appears to be on macrophages.
46 citations
40 citations
TL;DR: In this article, the reaction of 4-Dicyanomethylene-4H-pyrans with secondary amines gave copyrine and iminopyridone derivatives.
39 citations
TL;DR: The mass spectra of a series of hex-2-enopyranoside derivatives indicated that fragmentation of members of this class occurs by two general paths: (i) by loss of the substituents attached to C-1, C-4, and C-6, giving a series cyclic ions related to pyran, and (ii) by retrodienic cleavage as mentioned in this paper.
30 citations
Patent•
23 Mar 1970TL;DR: In this paper, the authors discuss the use of reaction at the 9 and/or 10 positions for anti-inflamMATORY and anti-proto-drug agents.
Abstract: 3-(LOWER ALKOXY)-7,8,9,10-TETRAHYDRO-6H-DIBENZO(B,D)PYRAN-6,9-DIONES ARE OBTAINED BY CYCLIZATION OF THE CORRESPONDING 7-(LOWER ALKOXY-4-METHYLCOUMARIN 3-PROPIONATE ESTERS. THE LATTER COMPOUNDS TOGETHER WITH DERIVATIVES OBTAINED BY REACTION AT THE 9 AND/OR 10 POSITIONS ARE USEFUL PHARMACOLOGICAL AGENTS, E.G. ANTI-INFLAMMATORY AND ANTI-PROTOZOAL.
21 citations
TL;DR: The reaction of o-phenolic Mannich bases with enamines yields cyclic O,N-acetals having a 2-aminodihydro-pyrans or a spiropyranopiperidine structure in common.
18 citations
Patent•
26 May 1970
TL;DR: In this article, the authors used a 2-R1,2''-R2-3,3''-SPIROBI(3H-NAPHTHO(2,1-B)PYRAN where R1 and R2 EACH is SELECTED from the groupconsisting of a HYDROGEN ATOM, an ALKYL GROUP HAVING from 1 to 8 CARBON ATOMS, A CARBOXYLIC ACID ESTER, AN ARALKYL GROUP and A PHENYL GROUP, a SOLID
Abstract: HEAT SENSITIVE COPYING PAPERS USING A SPIRO COMPOUND HAVING THE FORMULA A 2-R1,2''-R2-3,3''-SPIROBI(3H-NAPHTHO(2,1-B)PYRAN WHEREIN R1 AND R2 EACH IS SELECTED FROM THE GROUP CONSISTING OF A HYDROGEN ATOM, AN ALKYL GROUP HAVING FROM 1 TO 8 CARBON ATOMS, A CARBOXYLIC ACID ESTER, AN ARALKYL GROUP AND A PHENYL GROUP, A SOLID ORGANIC SULFONIC ACID HAVING THE FORMULA R-SO3H (B) WHEREIN R IS SELECTED FROM THE GROUP CONSISTING OF AN AMINO GROUP, AN N-SUBSTITUTED AMINO ALKYL GROUP HAVING FROM 2 TO 18 CARBON ATOMS, AN UNSUBSTITUTED AMINO ALKYL GROUP HAVING FROM 2 TO 18 CARBON ATOMS, AN ALKYL GROUP HAVING FROM 10 TO 20 CARBON ATOMS, AN ALKOXY GROUP HAVING FROM 10 TO 20 CARBON ATOMS, A CARBOXYLIC ACID SUBSTITUTED ALKYL GROUP, SAID ALKYL GROUP HAVING FROM 6 TO 18 CARBON ATOMS, AND AN AROMATIC RING, AND A THERMOFUSIBLE MATERIAL HAVING A MELTING POINT RANGING FROM 50 TO 180*C. ARE DISCLOSED.
16 citations
15 citations
TL;DR: Tetrahydro-4H-pyran-4-one has been prepared in a two-stage process from 3-chloropropionyl chloride, in 45% overall yield as discussed by the authors.
Abstract: Tetrahydro-4H-pyran-4-one has been prepared in a two-stage process from 3-chloropropionyl chloride, in 45% overall yield.
15 citations
15 citations
TL;DR: In this paper, 4-Dicyanomethylene-2-phenyl-4H-benzo[b]pyran, the corresponding thia-pyranonaphthyridine derivative, and 5-amino-6-cyano-2,8-diphenylpyrano[4,3,2-de] [1,6]naphTHyridine, respectively.
Patent•
22 Jul 1970TL;DR: In this article, a 3-SUBSTITUTED 6AB,4A-HYDROXY, ALKOXY OR ACYLOXY PERHYDROCYCLOPENTA(F)(1)BENZOPYRANS OR NAPHTHO(2,1-B)PYRAN.
Abstract: STEREO-SPECIFIC TOTAL SYNTHESIS OF STEROIDAL MATERIALS. 7-SUBSTITUTED 3-OXO-1-HEPTENES OR VARIANTS THEREOF ARE REACTED WITH 2-ALKYLCYCLOALKANE 1,3-DIONES YIELDING 3-SUBSTITUTED 6AB-ALKYL-CYCLOPENTA(F)(1)BENZOPYRANS OR NAPHTHO(2,1-B)PYRANS. THESE AE THEN SUBJECTED TO A SELECTIVE CATALYTIC HYDROGENATION FOLLOWED BY AN INTRODUCTION OF A HYDROXY, ALKOXY OR ACYLOXY GROUP AT THE 4A-POSITION TO PRODUCED A 3-SUBSTITUTED 6AB,4A-HYDROXY, ALKOXY OR ACYLOXY PERHYDROCYCLOPENTA(F)(1)BENZOYPRAN OR PERHYDRO NAPHTHO(2,1-B)PYRAN. THESE LATTER COMPOUNDS ARE THEN CONVERTED INTO 4- OR 5-(3-OXOALKYL)PERHYDROINDENE-5ONES OR PERHYDRONAPHTHALENE-6-ONES WHICH IN TURN CAN BE CONVERTED TO KNOWN STEROIDAL MATERIALS BY KNOWN METHODS.
TL;DR: In this paper, the structure and conformation of 3-Bromo-2,5-dimethoxy-5,6-dihydro-2H-pyran were proven by analysis of their 100MHz proton magnetic resonance spectra.
Abstract: 3-Bromo-2,5-dimethoxytetrahydropyran (2), obtained by bromomethoxylation of 3-methoxy-3,4-dihydro-2H-pyran (1), was dehydrohalogenated to cis-2,5-dimethoxy-5,6-dihydro-2H-pyran (3). The epoxide 5, derived from 3, was converted to methyl 4-O-methyl-α-DL-arabinopyranoside (7) by treatment with aqueous potassium hydroxide. The structure and conformation of 7 and of its diacetate 8 were proven by analysis of their 100 MHz proton magnetic resonance spectra. Subsequent comparison with an authentic sample of methyl 4-O-methyl-α-L-arabinopyranoside corroborated the structural assignment.
TL;DR: In this article, photolysis of 2,6-diphenyl-4H-pyran-4thione in dioxan results in desulphurization to give 2,2′,6,6′-tetraphenyl -4,4′-bi(pyranylidene).
Abstract: Photolysis of 2,6-diphenyl-4H-pyran-4-thione in dioxan results in desulphurization to give 2,2′,6,6′-tetraphenyl-4,4′-bi(pyranylidene).
Patent•
25 May 1970
TL;DR: In this article, the peracid may be prepared in situ by reacting hydrogen peroxide with a carboxylic acid, and it is shown that peracid can react in the presence of a CATALYST SUCH AS TUNGSTIC ACID, a PERACID with a CYCLIC DIOL SUCH as 1,1-DIMETHYLOL-3-CYCLOHEXENE, 2,2-DimETHylOL-5-NORBORNENE, and 2, 2-dimETHylol-3,
Abstract: 4-HYDROXYL-1-METHYLOL-6-OXA (3.2.1)-BICYCLO-OCTANE, 4-HYDROXY-1-METHYLOL-6-OXA (3.2.1.13,8)-TRICYCLO-NONANE, AND 4-HYDROXY-1-METHYLOL-6,8-DIOXA (3.2.1)-BICYCLO-OCTANE ARE PREPARED BY REACTING IN THE PRESENCE OF A CATALYST SUCH AS TUNGSTIC ACID, A PERACID WITH A CYCLIC DIOL SUCH AS 1,1-DIMETHYLOL-3-CYCLOHEXENE, 2,2-DIMETHYLOL-5-NORBORNENE, 2,2-DIMETHYLOL-3,4-DIHYDRO (2H) pyran. The peracid may be prepared in situ by reacting hydrogen peroxide with a carboxylic acid.
TL;DR: In this paper, a method for obtaining 4aminocoumarins by the reaction of 4-chloromethane with amines in dimethyl sulfoxide is proposed, and the mechanism of nucleophilic and substitution in position 4 of the coumarin system is discussed.
Abstract: A convenient method for obtaining 4-aminocoumarins by the reaction of 4-chlorocoumarin with amines in dimethyl sulfoxide is proposed. The reactions of 4-chlorocoumarin with CD3ONa in CD3OD and with [N-D1]piperidine, of [3-D1]-4-chlorocoumarin with CH3ONa in CH3OH and with aniline and n-butylamine and of 4-methoxycoumarin with CD3ONa in CD3OD have been studied and the mechanism of nucleophilic and substitution in position 4 of the coumarin system is discussed.
Patent•
09 Dec 1970
TL;DR: In this paper, MATSCHAPPIJ N.V. Heading C2C.1,215,066.14 Feb., 1969 [25 March, 1968], No. 14198/68.
Abstract: 1,215,066. Acrylamides. SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ N.V. 14 Feb., 1969 [25 March, 1968], No. 14198/68. Heading C2C. [Also in Division A5] Novel acrylamides of the general formula wherein R is an alkyl group; R 1 is H or an alkyl group; R 2 is an unsubstituted carbocyclic group or carbocyclic-amino radical or, when R 1 is H, R 2 may also be a substituted carbocyclic group; A is an optionally substituted carbocyclic or heterocyclic group; B is H or alkyl or A and B, together with the vinylene group to which they are attached, form a carbocyclic group, an optionally substituted furan ring in which the O-atom is adjacent to the C-atom bearing the group R or an optionally substituted benzofuran, oxazole, thiadiazole, triazole, pyran, thiapyran, or pyridine ring system or partially hydrogenated derivatives of these ring systems, with the proviso that when A is CH 3 , R 1 is H and B is alkyl, are prepared by the halogenation of the compound followed by reaction of the acyl halide produced with an amine R 1 R 2 NH. The reaction is preferably performed in benzene or chloroform using thionyl chloride as halogenating agent. Alternative methods for producing the novel compounds are (1) reacting an ester of the acid of Formula II with a metallo-derivative of an amine R 1 R 2 NH, e.g. a Mg Grignard reagent, and (2) reacting a carboxylic acid of Formula II with phenyl phosphazoanilide (giving R 2 = phenyl). Amongst numerous examples are the compounds 2,3 - dimethyl crotonanilide, 2- methyl - furan - 3 - carboxanilide, 3 - trifluoromethyl crotonanilide, 5 - methyl - 1,2,3 - hiadiazole - 4 - carboxanilide, 2 - methyl - 5,6 - dihydro - (4H) - 3 - (N - (4,5 - methylenedioxyphenyl) - carboxamide) and 2 - methyl - 5,6 - dihydro - (4H) - 3 - (N - phenylcarboxhydrazide). 2 - Methyl - 4,5 - dihydrofuran - 3 - carboxylic acid chloride is obtained by treating the corresponding acid with thionyl chloride. 2 - Methyl - 5,6 - dihydro - (4H) - thiapyran- 3-carboxanilide is obtained by reacting thionyl chloride and aniline with the corresponding acid.
TL;DR: In this article, aporphine alkaloids are synthesised in low yields by intramolecular oxidative coupling of appropriate diphenols, which involve migration of aralkyl rather than of aryloxy-groups.
Abstract: The title compounds have been synthesised in low yields by intramolecular oxidative coupling of appropriate diphenols. They rearrange in acetic anhydride containing a trace of sulphuric acid to give high yields of 2-acetoxyxanthen and 2-acetoxydibenz[b,f]oxepin respectively. These rearrangements, which are related to those giving rise to many aporphine alkaloids, involve migration of aralkyl rather than of aryloxy-groups. Syntheses of 2- and 3-acetoxyxanthen and of 2-acetoxydibenz[b,f]oxepin are described.
Patent•
10 Mar 1970TL;DR: The bromination of 6,7dibenzyloxy-3bromo-4-methylcoumarin has been used to give 6.7-Dihydroxy-3-methylbenzofuran-2-carboxylic acid as mentioned in this paper, which has been synthesized by the catalytic debenzylation of the latter compound.
Abstract: The bromination of 6,7-dibenzyloxy-4-methylcoumarin has given 6,7-dibenzyloxy-3-bromo-4-methylcoumarin and this has been converted by the Perkin reaction into 5, 6-dibenzyloxy-3-methylbenzofuran and its 2-carboxy derivative. 5, 6-Dihydroxy-3-methylbenzofuran-2-carboxylic acid has been synthesized by the catalytic debenzylation of the latter compound.
Patent•
25 May 1970
TL;DR: In this paper, the peracid may be prepared in situ by reacting hydrogen peroxide with a carboxylic acid, and it is shown that peracid can react in the presence of a CATALYST SUCH AS TUNGSTIC ACID, a PERACID with a CYCLIC DIOL SUCH as 1,1-DIMETHYLOL-3-CYCLOHEXENE, 2,2-DimETHylOL-5-NORBORNENE, and 2, 2-dimETHylol-3,
Abstract: 4-HYDROXYL-1-METHYLOL-6-OXA (3.2.1)-BICYCLO-OCTANE, 4-HYDROXY-1-METHYLOL-6-OXA (3.2.1.13,8)-TRICYCLO-NONANE, AND 4-HYDROXY-1-METHYLOL-6,8-DIOXA (3.2.1)-BICYCLO-OCTANE ARE PREPARED BY REACTING IN THE PRESENCE OF A CATALYST SUCH AS TUNGSTIC ACID, A PERACID WITH A CYCLIC DIOL SUCH AS 1,1-DIMETHYLOL-3-CYCLOHEXENE, 2,2-DIMETHYLOL-5-NORBORNENE, 2,2-DIMETHYLOL-3,4-DIHYDRO (2H) pyran. The peracid may be prepared in situ by reacting hydrogen peroxide with a carboxylic acid.
TL;DR: In this article, photolysis of pyran under acidic conditions affords the hydrocarbon 1,2-diphenylacenaphthylene (II): this unusual photodehydration seems to involve the triplet state of (I) and does not occur in the absence of acid.
Abstract: Photolysis of pyran (I) under acidic conditions affords the hydrocarbon 1,2-diphenylacenaphthylene (II): this unusual photodehydration seems to involve the triplet state of (I) and does not occur in the absence of acid.
TL;DR: In this article, the synthesis of 6-aryl-substituted pyran-2,4-diones by the acylation of various phenol ethers (anisole, phenol, veratrole) with citric and acetonedicarboxylic acids in the presence of polyphosphoric acid (PPA) has been studied.
Abstract: A new method for the synthesis of 6-aryl-substituted pyran-2,4-diones by the acylation of various phenol ethers (anisole, phenol, veratrole) with citric and acetonedicarboxylic acids in the presence of polyphosphoric acid (PPA) has been studied. The mechanism of the reaction and the spectra of the compounds obtained are discussed.
TL;DR: In this paper, the pyrylium cation is formed through the formation of a pyran which, with an excess of the initial pyrlium salt, splits out a hydride ion, aromatizing into a trisubstituted pyrn.
Abstract: Pyrylium salts having no substituents in position 4 react with aromatic and heteroaromatic compounds forming 4-aryl- and 4-heterylpyrylium derivatives. The reaction takes place through the stage of the formation of a pyran which, with an excess of the initial pyrylium salt, splits out a hydride ion, aromatizing into a trisubstituted pyrylium cation.