Category: 33402-75-4

Villani, Frank J.; Wefer, Elizabeth A.; Mann, Thomas A.; Mayer, Joseph; Peer, Lydia; Levy, Alfred S. published the artcile< Derivatives of 10, 11-dihydro-5H-benzo(a,d)cycloheptane and related compounds. VII. Improved syntheses of 11-H-benzo(5,6)cyclohepta(1,2-c)pyridin-11-one>, SDS of cas: 33402-75-4, the main research area is benzocycloheptapyridine; nicotinamide styryl thienyl; nicotinate styryl benzocycloheptapyridine.

An improved synthesis of the title compound (I) was described. The base-catalyzed condensation of 4-methylnicotinonitrile with PhCHO resulted in the isolation of trans-4-styrylnicotinamide (II, R = NH2) in high yield. Hydrolysis to II (R = OH) and heating with polyphosphoric acid gave I in good yields. Even higher yields of I were obtained in the presence of catalytic quantities of selenium. Also described are two other syntheses of the title compound and the preparation of a series of compounds related to II.

Journal of Heterocyclic Chemistry published new progress about Condensation reaction. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, SDS of cas: 33402-75-4.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Galenko, Ekaterina E.; Novikov, Mikhail S.; Shakirova, Firuza M.; Shakirova, Julia R.; Kornyakov, Ilya V.; Bodunov, Vladimir A.; Khlebnikov, Alexander F. published the artcile< Isoxazole Strategy for the Synthesis of 2,2'-Bipyridine Ligands: Symmetrical and Unsymmetrical 6,6'-Binicotinates, 2,2'-Bipyridine-5-carboxylates, and Their Metal Complexes>, Category: esters-buliding-blocks, the main research area is sym binicotinate bipyridine carboxylate metal complex preparation; unsym binicotinate bipyridine carboxylate metal complex preparation.

An effective strategy was developed for the synthesis of new 2,2′-bipyridine ligands, sym. and unsym. 6,6′-binicotinates, and 2,2′-bipyridine-5-carboxylates, from 4-propargylisoxazoles. The synthesis of sym. 2,2′-disubstituted 6,6′-binicotinates was achieved using the Eglinton reaction of 5-methoxy-4-(prop-2-yn-1-yl)isoxazoles with Cu(OAc)2, followed by Fe(NTf2)2/Au(NTf2)tBuXPhos-catalyzed isomerization of the so-formed mixture of isoxazole/azirine-substituted biacetylenic intermediates. Unsym. 2,2′-disubstituted 6,6′-binicotinates were prepared via a copper-free Sonogashira coupling of 5-methoxy-4-(prop-2-yn-1-yl)isoxazoles with 6-bromonicotinates to give Me 6-(3-(5-methoxyisoxazol-4-yl)prop-1-ynyl)pyridine-3-carboxylates, followed by a transformation of the propargylisoxazole moiety of the adduct into the pyridine fragment under Fe(II)/Au(I) relay catalysis conditions. 6-(Pyrid-2-yl)nicotinates were synthesized by a Stille-type coupling of 2-(tributylstannyl)pyridine with 6-bromonicotinates. Several cyclopalladated complexes of a new series of 6,6′-binicotinates and 2,2′-bipyridine-5-carboxylates and the homoleptic Cu(I) complex were synthesized in high yields.

Journal of Organic Chemistry published new progress about Crystal structure. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Category: esters-buliding-blocks.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Shariff, Azim; McLean, Stewart published the artcile< The synthesis of Nauclea indole-pyridine alkaloids. 3,4-Disubstituted and 3,4,5-trisubstituted pyridines as synthetic intermediates; a total synthesis of (±)-decarbomethoxy-3α- and -3β-nauclechine>, Quality Control of 33402-75-4, the main research area is nauclechine decarbomethoxy epimer synthesis; pyridine substituted; pyridineacetic acid substituted Bischler Napieralski; Nauclea indole pyridine alkaloid.

Synthetic routes to a number of 3,4-disubstituted and 3,4,5-trisubstituted pyridines was explored. These pyridines, designed to be used in the synthesis of Nauclea indole-pyridine alkaloids, are potentially useful intermediates in a number of syntheses. Substituted 4-pyridineacetic acids were prepared and the exptl. limitations associated with their synthesis and use in subsequent reactions such as the Bischler-Napieralski cyclization were discussed. A synthesis of decarbomethoxynauclechine from 4-methylnicotinaldehyde avoiding these difficulties was described. (±)-Decarbomethoxy-3α-nauclechine (I; R = α-H) and (±)-decarbomethoxy-3β-nauclechine (I; R = β-H) were obtained and their structure and stereochem. were established, but it was not possible to demonstrate which corresponded to the natural alkaloid, decarbomethoxynauclechine.

Canadian Journal of Chemistry published new progress about Alkaloids Role: SPN (Synthetic Preparation), PREP (Preparation). 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Quality Control of 33402-75-4.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Rombouts, Frederik J. R.; Tresadern, Gary; Buijnsters, Peter; Langlois, Xavier; Tovar, Fulgencio; Steinbrecher, Thomas B.; Vanhoof, Greet; Somers, Marijke; Andres, Jose-Ignacio; Trabanco, Andres A. published the artcile< Pyrido[4,3-e][1,2,4]triazolo[4,3-a]pyrazines as Selective, Brain Penetrant Phosphodiesterase 2 (PDE2) Inhibitors>, Computed Properties of 33402-75-4, the main research area is pyrido triazolo pyrazine brain phosphodiesterase inhibitor; PDE2 inhibitor; Pyrido[4,3-e][1,2,4]triazolo[4,3-a]pyrazine; phosphodiesterase 2 inhibitor; selective; tricycle.

A novel series of pyrido[4,3-e][1,2,4]triazolo[4,3-a]pyrazines is reported as potent PDE2/PDE10 inhibitors with drug-like properties. Selectivity for PDE2 was obtained by introducing a linear, lipophilic moiety on the meta-position of the Ph ring pending from the triazole. The SAR and protein flexibility were explored with free energy perturbation calculations Rat pharmacokinetic data and in vivo receptor occupancy data are given for two representative compounds 6 and 12.

ACS Medicinal Chemistry Letters published new progress about Drug bioavailability. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Computed Properties of 33402-75-4.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Seeman, Jeffrey I.; Secor, Henry V.; Chavdarian, Charles G.; Sanders, Edward B.; Bassfield, Ronald L.; Whidby, Jerry F. published the artcile< Steric and conformational effects in nicotine chemistry>, Computed Properties of 33402-75-4, the main research area is alkylation kinetics nicotine; nicotine indomethylation stereochem; conformation indomethylation nicotine; NMR carbon 13 iodomethylated nicotine.

The stereoselectivity of iodomethylation of nicotine and 7 nicotine analogs having pyridine alkyl groups was determined by using 13C NMR. Alkylation at the pyridine (N) and at the pyrrolidine (N’) nitrogens was observed Two modes of N’-iodomethylation occur, cis and trans to the pyridine ring. N’-Iodomethylation occurs regioselectivity cis to the pyridine ring for all compounds examined The N/N’ and N’cis/N’trans ratios for the nicotine analogs were evaluated with regard to the orientation of the N’-Me group in the free base, conformational properties of the pyridine ring with respect to the pyrrolidine ring, and steric hindrance and buttressing effects on the pyridine nitrogen. The Curtin-Hammett principle and the Winstein-Holness equation are used to analyze these reactions.

Journal of Organic Chemistry published new progress about Alkaloids Role: RCT (Reactant), RACT (Reactant or Reagent). 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Computed Properties of 33402-75-4.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Wenkert, Ernest; Sprague, P. W.; Webb, R. L. published the artcile< General methods of synthesis of indole alkaloids. XII. Synthesis of dl-18,19-dihydroantirhine and methyl demethylilludinate>, Recommanded Product: Methyl 4-methylnicotinate, the main research area is indole alkaloid; illudinininate demethyl; antirhine dihydro; pyridine alkaloid; demethylilludinininate methyl; dihydroantirhine.

Methyl nicotinate I (R = R1 = H) was condensed with MeCHO to give I (RR1 = MeCH:) and with 3,3-dimethylcyclopentanone to give I, (RR1 = 3,3-dimethylcyclopentylidene). Reduction, and oxidation of the I (RR1 = MeCH:) led to lactone II and thence in 3 steps to an antirhine derivative (±)III. Esterification and cyclization of I (RR1 = 3,3-dimethylcyclopentylidene) afforded an illudinine derivative IV.

Journal of Organic Chemistry published new progress about Alkaloids. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Recommanded Product: Methyl 4-methylnicotinate.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Sugimori, Akira; Tobita, Etsuo; Kumagai, Yasuyuki; Sato, Gen P. published the artcile< Multiple paths for photo-alkylation and -alkoxylation of 3-pyridinecarboxylic ester in alcohol. Simultaneous contribution of several kinds of excited states>, Electric Literature of 33402-75-4, the main research area is photochem alkylation alkoxylation pyridinecarboxylate.

UV irradiation of Me 3-pyridinecarboxylate (I) in acidic alc. solutions causes alkoxylation and alkylation at the pyridine ring. Photoalkylation occurs via several paths: 1) initiated by the triplet π-π* state; 2) initiated by the triplet n-π* state of the carbonyl moiety of the ester group; 3) initiated by an exciplex between a free-base form of I and a pyridinium form of I; and 4) promoted by Cl- ions. Photoalkoxylation originates from a singlet excited state of I. In the photoreactions of I in strongly acidic MeOH solutions acidified with H2SO4, 3 kinds of excited states (2 kinds of triplet states for alkylation and a singlet state for alkoxylation) contribute simultaneously.

Bulletin of the Chemical Society of Japan published new progress about Photochemical alkylation. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Electric Literature of 33402-75-4.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Dunn, A. D. published the artcile< Synthesis of new thiopyranopyridines>, Quality Control of 33402-75-4, the main research area is thiopyranopyridinecarboxylate; photochem bromination pyridinecarboxylate; bromomethylpyridinecarboxylate preparation substitution thioglycolate.

Thiopyranopyridinecarboxylates I and II (X, Y = CH, N; R = OH, NH2) are prepared from pyridine esters (e.g., III; R1 = Me, R2 = CO2Me; R1 = CO2Me, R2 = Me) and nitriles (e.g., III; R1 = Me, R2 = CN) by photochem. bromination, followed by substitution reaction of the resulting bromomethyl derivative with HSCH2CO2Me, and then base-induced intramol. cyclocondensation.

Journal fuer Praktische Chemie (Leipzig) published new progress about Cyclocondensation reaction, intramolecular. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Quality Control of 33402-75-4.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Sugimori, Akira; Tobita, Etsuo; Kumagai, Yasuyuki; Sato, Gen P. published the artcile< Multiple paths for photo-alkylation and -alkoxylation of 3-pyridinecarboxylic ester in alcohol. Simultaneous contribution of several kinds of excited states>, Electric Literature of 33402-75-4, the main research area is photochem alkylation alkoxylation pyridinecarboxylate.

UV irradiation of Me 3-pyridinecarboxylate (I) in acidic alc. solutions causes alkoxylation and alkylation at the pyridine ring. Photoalkylation occurs via several paths: 1) initiated by the triplet π-π* state; 2) initiated by the triplet n-π* state of the carbonyl moiety of the ester group; 3) initiated by an exciplex between a free-base form of I and a pyridinium form of I; and 4) promoted by Cl- ions. Photoalkoxylation originates from a singlet excited state of I. In the photoreactions of I in strongly acidic MeOH solutions acidified with H2SO4, 3 kinds of excited states (2 kinds of triplet states for alkylation and a singlet state for alkoxylation) contribute simultaneously.

Bulletin of the Chemical Society of Japan published new progress about Photochemical alkylation. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Electric Literature of 33402-75-4.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Dunn, A. D. published the artcile< Synthesis of new thiopyranopyridines>, Quality Control of 33402-75-4, the main research area is thiopyranopyridinecarboxylate; photochem bromination pyridinecarboxylate; bromomethylpyridinecarboxylate preparation substitution thioglycolate.

Thiopyranopyridinecarboxylates I and II (X, Y = CH, N; R = OH, NH2) are prepared from pyridine esters (e.g., III; R1 = Me, R2 = CO2Me; R1 = CO2Me, R2 = Me) and nitriles (e.g., III; R1 = Me, R2 = CN) by photochem. bromination, followed by substitution reaction of the resulting bromomethyl derivative with HSCH2CO2Me, and then base-induced intramol. cyclocondensation.

Journal fuer Praktische Chemie (Leipzig) published new progress about Cyclocondensation reaction, intramolecular. 33402-75-4 belongs to class esters-buliding-blocks, and the molecular formula is C8H9NO2, Quality Control of 33402-75-4.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics