14203-46-4Relevant articles and documents
SOLID FORMS OF 2-(TERT-BUTYLAMINO)-4-((1R,3R,4R)-3-HYDROXY-4-METHYLCYCLOHEXYLAMINO)-PYRIMIDINE-5-CARBOXAMIDE, COMPOSITIONS THEREOF AND METHODS OF THEIR USE
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Paragraph 00464, (2015/11/02)
Provided herein are formulations, processes, solid forms and methods of use relating to 2- (tert-butylamino)-4-((lR,3R,4R)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5- carboxamide.
One-pot synthesis of fused pyrroles through a key gold-catalysis-triggered cascade
Zheng, Zhitong,Tu, Huangfei,Zhang, Liming
supporting information, p. 2445 - 2448 (2014/03/21)
A two-step, one-pot synthesis of fused pyrroles is realized by firstly condensing an N-alkynylhydroxammonium salt with a readily enolizable ketone under mild basic conditions and then subjecting the reaction mixture to a gold catalyst, which triggers a cascade reaction involving a facile initial [3.3]-sigmatropic rearrangement of the gold-catalysis product, that is, an N,O-dialkenylhydroxamine. The reaction provides a facile access to polycyclic pyrroles in moderate to good yields. A two-step, one-pot synthesis of fused pyrroles is realized by firstly condensing an N-alkynylhydroxammonium salt with a readily enolizable ketone under mild basic conditions and then subjecting the reaction mixture to a gold catalyst, which triggers a cascade reaction involving a facile initial [3.3]-sigmatropic rearrangement of the gold-catalysis product, that is, an N,O-dialkenylhydroxamine. The reaction provides a facile access to polycyclic pyrroles in moderate to good yields (see scheme). Copyright
SUBSTITUTED CYCLOHEXANE-1, 3-DIONE COMPOUNDS, PROCESS FOR PREPARATION THEREOF AND ITS APPLICATIONS
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Paragraph 0051, (2013/04/10)
A regio-selective and consecutive Michael-Claisen process has been developed for substituted cyclohexane-1,3-dione synthesis started from unsubstituted or substituted acetone and α,β-unsaturated esters. Substituted cyclohexane-1,3-diones are the basic uni
Consecutive Michael-claisen process for cyclohexane-1,3-dione derivative (CDD) synthesis from unsubstituted and substituted acetone 1
Sharma, Dharminder,Shil, Arun K.,Singh, Bikram,Das, Pralay
supporting information; experimental part, p. 1199 - 1204 (2012/06/15)
A long-existing problem of cyclohexane-1,3-dione derivatives (CDD) synthesis from unreactive acetone through consecutive Michael-Claisen process was solved under this study. The practical applicability of this process was tested for a novel compound ethyl 3-(2,4-dioxocyclohexyl)propanoate for up to 20-gram scale. Furthermore, the scope of different acetone derivatives was investigated and resulted with similar consecutive Michael-Claisen process for CDD synthesis. The reaction exhibited remarkable regioselectivity in Michael addition followed by Claisen cyclization. In this process high substrate selectivity was observed for CDD synthesis following consecutive double-Michael-Claisen and Michael-Claisen cyclization. Georg Thieme Verlag Stuttgart · New York.
Tandem reactions leading to benzo[c]chromen-6-ones and 3-substituted isocoumarins
Fan, Xuesen,He, Yan,Cui, Liangyan,Guo, Shenghai,Wang, Jianji,Zhang, Xinying
supporting information; experimental part, p. 673 - 677 (2012/03/10)
A simple and convenient protocol for the synthesis of benzo[c]chromen-6- ones and 3-substituted isocoumarins through a CuI-catalyzed tandem reaction of 2-bromobenzoates withcyclohexane-1,3-diones or acyclic 1,3-diones is developed. This strategy can also be extended to the one-pot synthesis of isoquinolin-1(2H)-one and 3,4-dihydrophenanthridine-1,6(2H,5H)-dione. A simple and convenient protocol for the synthesis of benzo[c]chromen-6-ones and 3-substituted isocoumarins through a CuI-catalyzed tandem reaction of 2-bromobenzoates with cyclohexane-1,3-dione or acyclic 1,3-dione has been developed. This strategy can also be extended to the one-pot synthesis of isoquionlin-1(2H)-one and 3,4-dihydrophenanthridine-1,6-(2H,5H)-dione. Copyright
SUBSTITUTED CYCLOHEXANE-1, 3-DIONE COMPOUNDS, PROCESS FOR PREPARATION THEREOF AND ITS APPLICATIONS
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Page/Page column 12-13, (2011/10/13)
A regio-selective and consecutive Michael-Claisen process has been developed for substituted cyclohexane-1,3-dione synthesis started from unsubstituted or substituted acetone and α,β- unsaturated esters. Substituted cyclohexane-1,3-diones are the basic un
Synthesis and spectroscopic characterization of [5-13C]- and [6-13C]ubiquinone-10 for studies of bacterial photosynthetic reaction centers
Boers, Rutger B.,Gast, Peter,Hoff, Arnold J.,De Groot, Huub J. M.,Lugtenburg, Johan
, p. 189 - 202 (2007/10/03)
This paper presents the synthesis and characterization by mass spectrometry and NMR spectroscopy of [2-13C]- and [3-13C]ubiquinone-0 and of [5-13C]- and [6-13C]ubiquinone-10. A scheme based on the synthetic approach to [5-13C]ubiquinone-10 has been worked out for the synthesis of ubiquinones 13C-labeled at any individual position and at every combination of positions in the quinone ring. The [5-13C]- and [6-13C]ubiquinone-10 isotopomers were incorporated into the QA-site of the photosynthetic reaction center of Rhodobacter sphaeroides R-26. Magic angle spinning NMR subsequently revealed an unperturbed 6-position, while the signal of the 5-position was absent. These results corroborate the recently reported detection of an asymmetric binding of QA with a dynamic perturbation involving the 4-carbonyl functionality.
Revisiting [3 + 3] route to 1,3-cyclohexanedione frameworks: Hidden aspect of thermodynamically controlled enolates
Ishikawa, Teruhiko,Kadoya, Ryuichiro,Arai, Masaki,Takahashi, Haruka,Kaisi, Yumi,Mizuta, Tomohiro,Yoshikai, Kazusa,Saito, Seiki
, p. 8000 - 8009 (2007/10/03)
We have revisited the traditional consecutive Michael-Claisen [3 + 3] process (MC-[3+3]) promising the synthesis of a cyclohexane-1,3-dione derivatives from nonactivated simple ketones and enoates and evaluated its potential in modern organic synthesis. Twenty to thirty examples were demonstrated to be effective. The reactions exhibited remarkable regioselectivity with the Michael addition proceeding through nucleophilic attack by the more hindered site of the ketones without exception. The subsequent Claisen condensation resulted in the formation of carbon-carbon bonds between less hindered site of the ketones and acyl carbon of the enoates. The MC-[3+3] process described is useful for the synthesis of Taxol A-ring synthons in multigram quantities and for the synthesis of other six-membered carbocyclic compounds. A number of control experiments have been conducted to provide strong support for the mechanism of this MC-[3+3].
Regioselective alkylations of cyclic 1,3-diketones via metalated dimethylhydrazones
Demir, Ayhan S.,Enders, Dieter
, p. 553 - 563 (2007/10/03)
Cyclic 1,3- diketones 1 are transformed into their 2,2-dimethylhydrazones 2, which can be alkylated regioselectively at different positions after mono-, di-, tri-, and tetrametalation. Monometalated C-2 unsubstituted hydrazones afford C-2 and N- alkylation, monometalated C-2 substituted hydrazones afford only C-2 alkylation.The regioselectivity of the alkylation of the polymetalated hydrazones follows Hauser's rule according to the sequence: NH- > C-4 Ha > C-5 > C-4 Hb. Hydrolysis of the product hydrazones 3-5 afforded mono- and polyalkylated 1,3- diketones 7 in good yields.
Chiral acetals in organic synthesis: Regioselective synthesis of 2-and 3-hydroxy acetals from 2,3-olefinic acetals. Reinvestigation and further applications
Vankar, Yashwant D.,Reddy, M. Venkatram,Chaudhuri, Narayan C.
, p. 11057 - 11078 (2007/10/02)
Achiral as well as chiral 2,3-olefinic acetals are converted into 2- and 3- hydroxy acetals via LAH reduction of the corresponding epoxides and via bromohydrins followed by TBTH reductions respectively. Synthesis of 1,3-diones is described. Compounds from chiral systems are further utilized for asymmetric synthesis.
