Category: 89324-17-4

Bowman, W. Russell; Bridge, Colin F.; Cloonan, Martin O.; Leach, David C. published the artcile< Synthesis of heteroarenes via radical cyclisation onto nitriles>, Formula: C6H4N2O, the main research area is camptothecin ring system preparation cascade radical cyclization; indolizinoquinolinone preparation cascade radical cyclization.

A new protocol for the synthesis of tetracyclic nitrogen heteroarenes using cascade radical cyclization has been developed. The key steps involve 5-exo vinyl radical cyclization onto nitriles to yield intermediate iminyl radicals which cyclize onto an arene rings. Rings A-D (I) of the anticancer alkaloids camptothecin, mappicine and nothapodytines A and B have been synthesized using this protocol.

Synlett published new progress about Alkaloids Role: SPN (Synthetic Preparation), PREP (Preparation) (indolizinoquinolinone). 89324-17-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H4N2O, Formula: C6H4N2O.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kuzuya, Masayuki; Noguchi, Akihiro; Okuda, Takachiyo published the artcile< Quantum chemical consideration of substituent effects on tautomeric properties of 2-pyridones-2-pyridinols>, Reference of 89324-17-4, the main research area is tautomerism pyridone pyridinol UV; MO tautomerism pyridone; substituent effect pyridone tautomerism.

The tautomeric properties of 2-pyridones-2-pyridinols exerted by the substituent effect were discussed on the basis of quantum chem. quantities deduced from MO calculations A substituent at the 6-position has the greatest stabilizing effect. The magnitude of this effect was greater on the 2-pyridinol form than on the 2-pyridone form, irresp. of the nature of the substituent. This led to a large predominance of the 2-pyridinol form on the 6-polar-substituted derivatives, to such an extent that it was observed by conventional UV measurements at ambient temperature In the 6-Me derivative, the 2-pyridinol form was not observed by a similar measurement due to the weak substituent effect. The association ability is still an important factor in determining tautomeric equilibrium in a solution, resulting in a strong lability to the mol. environment. The substituent effects on the stabilities of both tautomers were correlated with the N-at. charges and ring structural modifications of the tautomers.

Bulletin of the Chemical Society of Japan published new progress about Electron configuration. 89324-17-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H4N2O, Reference of 89324-17-4.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ben Messaouda, M.; Mahjoub, A.; Mogren Al-Mogren, M.; Abderrabba, M.; Hochlaf, M. published the artcile< Substituent effects on vibrational and electronic excitation spectra of pyridone tautomers and ions: The case of the cyano group>, Electric Literature of 89324-17-4, the main research area is substituent effect vibrational electronic excitation spectra cyano substituted pyridone.

In this theor. work, we computed the equilibrium geometries and a set of rotational and vibrational spectroscopic parameters for cyano substituted 2-pyridones neutral or cationic and their tautomers (cyano 2-hydroxypyridines). We examined also the effect of tautomerism equilibrium on those systems. In our anal., we mostly focused on the perturbations induced by the CN group on the electronic structure and on the spectroscopy of 2-pyridone/2-hydroxypyridine block. Moreover, we investigated the pattern of their low lying electronic states at both the PBE0/aug-cc-pVDZ D. Functional Theory (DFT) and the CASSCF/aug-cc-pVTZ levels of theory. Vertical excitation spectra and both adiabatic and vertical ionization energies were performed.

Journal of Molecular Structure published new progress about Adiabatic ionization potential. 89324-17-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H4N2O, Electric Literature of 89324-17-4.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Bowman, W. Russell; Bridge, Colin F.; Brookes, Philip; Cloonan, Martin O.; Leach, David C. published the artcile< Cascade radical synthesis of heteroarenes via iminyl radicals>, Computed Properties of 89324-17-4, the main research area is radical cyclization iminyl vinyl nitrile heteroarene preparation; heteroarene alkaloid tetracycle indolizinoquinolinone ring preparation; cyclization radical reaction mechanism iminyl.

A novel cascade cyclization protocol has been developed which ‘zips up’ two rings to form new tetracycles. In the protocol, treatment of vinyl bromides and iodides with hexamethylditin radicals yields intermediate vinyl radicals which undergo 5-exo cyclization onto nitrile groups to yield intermediate iminyl radicals. The iminyl radicals can undergo 6-endo cyclization (or 5-exo followed by neophyl rearrangement) to yield tetracyclic π-radicals which lose hydrogen radical in an H-abstraction step. Me radicals, generated from the breakdown of trimethylstannyl radicals, are proposed as a possible H-abstractor for this final oxidative step. The protocol has been used to synthesize the tetracyclic rings A-D (tetracycle indolizino[1,2-b]quinolin-9(11H)-one) of the anticancer alkaloids camptothecin, mappicine, nothapodytine B and nothapodytine A. The protocol has also been applied to the synthesis of analogs of camptothecin in which ring A has been replaced by thiophene (8,10-dihydrothieno[2′,3′:5,6]pyrido[2,3-a]indolizin-8-one) and ring D by pyrrole (10H-pyrrolizino[1,2-b]quinoline) and benzene (11H-indeno[1,2-b]quinolin-11-one).

Journal of the Chemical Society, Perkin Transactions 1 published new progress about Alkaloids Role: SPN (Synthetic Preparation), PREP (Preparation) (tetracyclic). 89324-17-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H4N2O, Computed Properties of 89324-17-4.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Dai, Weixiang; Petersen, Jeffrey L.; Wang, Kung K. published the artcile< Synthesis of the Parent and Substituted Tetracyclic ABCD Ring Cores of Camptothecins via 1-(3-Aryl-2-propynyl)- 1,6-dihydro-6-oxo-2-pyridinecarbonitriles>, Related Products of 89324-17-4, the main research area is camptothecin ABCD ring core preparation nitrogen alkylation Curran’s protocol; intramol hetero Diels Alder acetylene allene rearrangement radical cyclization; radical cyclization reaction mechanism camptothecin core preparation; crystal mol structure indolizinoquinolinone camptothecin ring core analog.

A new synthetic pathway to the parent and substituted ABCD ring cores, e.g. I, of the camptothecin family of alkaloids was developed. The N-alkylation of 1,6-dihydro-6-oxo-2-pyridinecarbonitrile with 3-bromo-1-phenylpropyne provided II using Curran’s protocol. Treatment of II with a catalytic amount of DBU (5 mol %) at 110 °C for 12 h produced indolizino[1,2-b]quinolin-9(11H)-one (I), the parent ABCD ring core of camptothecin, in essentially quant. yield.

Organic Letters published new progress about Alkaloids Role: SPN (Synthetic Preparation), PREP (Preparation). 89324-17-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H4N2O, Related Products of 89324-17-4.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Yukawa, Tomoya; Nakada, Yoshihisa; Sakauchi, Nobuki; Kamei, Taku; Yamada, Masami; Ohba, Yusuke; Fujimori, Ikuo; Ueno, Hiroyuki; Takiguchi, Maiko; Kuno, Masako; Kamo, Izumi; Nakagawa, Hideyuki; Fujioka, Yasushi; Igari, Tomoko; Ishichi, Yuji; Tsukamoto, Tetsuya published the artcile< Design, synthesis, and biological evaluation of a novel series of peripheral-selective noradrenaline reuptake inhibitors - Part 3>, Category: nitriles-buliding-blocks, the main research area is crystal structure noradrenaline reuptake inhibitor urinary incontinence; 7-Aryl-1,4-oxazepane derivatives; Intramolecular hydrogen bond; MDR1 efflux ratio; Peripheral-selective noradrenaline reuptake inhibitor; Stress urinary incontinence.

Peripheral-selective inhibition of noradrenaline reuptake is a novel mechanism for the treatment of stress urinary incontinence to overcome adverse effects associated with central action. Here, the authors describe the medicinal chem. approach to discover a novel series of highly potent, peripheral-selective, and orally available noradrenaline reuptake inhibitors with a low multidrug resistance protein 1 (MDR1) efflux ratio by cyclization of an amide moiety and introduction of an acidic group. The authors observed that the MDR1 efflux ratio was correlated with the pKa value of the acidic moiety. The resulting compound I exhibited favorable PK profiles, probably because of the effect of intramol. hydrogen bond, which was supported by a its single-crystal structure. Compound I, which exhibited peripheral NET-selective inhibition at tested doses in rats by oral administration, increased urethral resistance in a dose-dependent manner.

Bioorganic & Medicinal Chemistry published new progress about Antidiuretics. 89324-17-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H4N2O, Category: nitriles-buliding-blocks.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Alhatem, Aamer A. published the artcile< Tautomeric equilibria of substituted 2-pyridone/2-hydroxypyridine in the gas and aqueous phases>, Application of C6H4N2O, the main research area is pyridone hydroxypyridine tautomer substituent effects formation enthalpy free energy.

Heats of formation, entropies and Gibbs free energies for the twenty structures of substituted 2-pyridone and 2-hydroxypyridine were studied using semiempirical Austin Model (AM1) and Parametric Method 3 (PM3) calculations at the SCF level, both in the gas and liquid phases, with full geometry optimization. It was revealed from the study that 2-hydroxypyridine is predominant in gas phase, while 2-pyridone in the liquid phase which agrees with the exptl. and theor. predictions. All substituents such as F, Cl, OH, CH3, NH2, NO2, CHO, CN, CF3 stabilize the 2-pyridone in the gas and liquid phases except F, Cl and NH2 in PM3 calculations in the gas phase. The substituents stabilization is more effective in liquid phase. This was also confirmed by thermodn. calculations and isodesmic reactions.

Chemical Science International Journal published new progress about Entropy. 89324-17-4 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H4N2O, Application of C6H4N2O.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts