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You searched for: Journal Journal of organic chemistry Remove constraint Journal: Journal of organic chemistry Publication Year 2018 Remove constraint Publication Year: 2018 Source 2018 v.83 no.24 Remove constraint Source: 2018 v.83 no.24
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1. Three-Component Coupling of Aldehydes, Aminopyrazoles, and Sulfoxonium Ylides via Rhodium(III)-Catalyzed Imidoyl C–H Activation: Synthesis of Pyrazolo[1,5-a]pyrimidines

Author:
Hoang, Gia L.; Streit, Andrew D.; Ellman, Jonathan A.
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15347-15360
ISSN:
1520-6904
Subject:
aldehydes; carbon-hydrogen bond activation; chemical reactions; moieties; nitrogen; organic chemistry; pyrimidines; rhodium
Abstract:
... An efficient, three-component strategy for Rh(III)-catalyzed annulation of readily available 3-aminopyrazoles, aldehydes, and sulfoxonium ylides to give diverse pyrazolo[1,5-a]pyrimidines is disclosed. The reactions were performed under straightforward benchtop conditions using microwave heating with short reaction times. Good yields were obtained for many substituted aminopyrazoles and a very lar ...
DOI:
10.1021/acs.joc.8b02606

2. Total Solid-Phase Synthesis of Dehydroxy Fengycin Derivatives

Author:
Rosés, Cristina; Camó, Cristina; Oliveras, Àngel; Moll, Lluis; López, Nerea; Feliu, Lidia; Planas, Marta
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15297-15311
ISSN:
1520-6904
Subject:
acylation; amino acid composition; esterification; moieties; organic chemistry; phenol
Abstract:
... A rapid and efficient solid-phase strategy for the synthesis of dehydroxy fengycins derivatives is described. This synthetic approach involved the linkage of a Tyr to a Wang resin via a Mitsunobu reaction and the elongation of the peptide sequence followed by subsequent acylation of the N-terminus of the resulting linear peptidyl resin, esterification of the phenol group of a Tyr with an Ile, and ...
DOI:
10.1021/acs.joc.8b02553

3. Contemporary Synthetic Strategies toward seco-Prezizaane Sesquiterpenes from Illicium Species

Author:
Condakes, Matthew L.; Novaes, Luiz F. T.; Maimone, Thomas J.
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 14843-14852
ISSN:
1520-6904
Subject:
Illicium; carbon; chemical reactions; chemical structure; chemists; organic chemistry; sesquiterpenoid lactones
Abstract:
... Since the elucidation of the structure of anisatin in the late 1960s, sesquiterpene lactones from various Illicium species of plants have captivated synthetic chemists worldwide, resulting in a large body of synthetic work. In particular, Illicium sesquiterpenes containing the seco-prezizaane carbon framework have seen immense interest in recent years owing to desirable structural and medicinal at ...
DOI:
10.1021/acs.joc.8b02802

4. Synthesis of Protected Amino Hexitol Nucleosides as Building Blocks for Oligonucleotide Synthesis

Author:
De, Swarup; Jabgunde, Amit M.; Patil, Rahul S.; De Jonghe, Steven; Beigelman, Leonid; Herdewijn, Piet
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15155-15169
ISSN:
1520-6904
Subject:
azides; chemical reactions; chemical structure; ethylene oxide; nucleic acids; nucleosides; oligonucleotides; organic chemistry; regioselectivity; uracil
Abstract:
... A new synthesis protocol for the preparation of hitherto unknown 1′,5′-anhydro-4′-amino-trityl/MMTr hexitol nucleosides has been developed. Key steps in the synthesis of the pyrimidine analogues (U and C) include the regioselective d-allo-hexitol oxirane and 2′,4′-anhydronucleoside ring opening by uracil and azide, respectively. A different strategy using a regioselective epoxide ring opening of d ...
DOI:
10.1021/acs.joc.8b02444

5. One-Pot Synthesis of 2-Styrylindoles from Ortho-Substituted Chloroenynes

Author:
Zhao, Guangkuan; Bignon, Jerôme; Levaique, Helène; Dubois, Joëlle; Alami, Mouad; Provot, Olivier
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15323-15332
ISSN:
1520-6904
Subject:
antineoplastic activity; arylation; chemical structure; organic chemistry; organic compounds; synthesis
Abstract:
... A facile one-pot synthesis of 2-styrylindoles, through Suzuki arylation of ortho-substituted chloroenynes followed by N-cyclization and N-demethylation, has been developed. A variety of 2-styrylindoles were obtained in good to excellent yields and were evaluated for their anticancer properties. ...
DOI:
10.1021/acs.joc.8b02563

6. Chemoselective Aza-[4+3]-annulation of N-Perfluoroalkyl-1,2,3-triazoles with 1,3-Dienes: Access to N-Perfluoroalkyl-Substituted Azepines

Author:
Motornov, Vladimir; Beier, Petr
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15195-15201
ISSN:
1520-6904
Subject:
chemical reactions; chemical structure; chemoselectivity; microwave treatment; organic chemistry; regioselectivity; triazoles
Abstract:
... Rhodium-catalyzed transannulation of N-perfluoroalkylated 1,2,3-triazoles with 1,3-dienes under microwave heating proceeded chemoselectively via the formal aza-[4+3]-pathway, affording N-perfluoroalkyl-substituted 2,5-dihydroazepines. A unique regioselectivity profile was observed in annulation with 1-substituted 1,3-diene, affording unusual 5,6-disubstituted examples. Transannulation of triazoles ...
DOI:
10.1021/acs.joc.8b02472

7. One-Pot Synthesis of 4-Sulfonyliminotetrahydropyrimidin-2-one Derivatives through a Copper-Catalyzed Tandem Reaction

Author:
Tong, Tao; Wu, Xin; Li, Erfei; Kang, Honglan; Wang, Xiaoxia; Lv, Xin
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15533-15540
ISSN:
1520-6904
Subject:
azides; chemical reactions; chemical structure; copper; organic chemistry; synthesis
Abstract:
... A novel and efficient synthesis of 4-iminotetrahydropyrimidin-2-one derivatives was developed through a Cu(I)-catalyzed three-component tandem reaction employing propargylamines, isocyanates, and sulfonyl azides as starting materials. A wide range of polysubstituted 4-sulfonyliminotetrahydropyrimidin-2-ones, which might be useful in biological chemistry and medicinal science, were conveniently and ...
DOI:
10.1021/acs.joc.8b02642

8. Copper-Catalyzed Coupling Reactions of Cyclobutanone Oxime Esters with Sulfur Nucleophiles at Room Temperature

Author:
He, Mingchuang; Yan, Zhaohua; Zhu, Fuyuan; Lin, Sen
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15438-15448
ISSN:
1520-6904
Subject:
Lewis bases; ambient temperature; chemical bonding; chemical structure; copper; esters; imines; organic chemistry; photocatalysis; sulfides; sulfur; thiols
Abstract:
... A copper-catalyzed iminyl radical-mediated C–C bond cleavage/cross-coupling tandem reaction of cyclobutanone oxime esters with aryl thiols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) at room temperature was developed, and aryl cyanopropyl sulfides were smoothly synthesized in 20–88% yields. By altering the copper reagent and the molar ratio of cyclobutanone oxime ester/aryl thiol/D ...
DOI:
10.1021/acs.joc.8b02707

9. Reaction of Aromatic Carbonyl Compounds with Silylborane Catalyzed by Au Nanoparticles: Silylative Pinacol-type Reductive Dimerization via a Radical Pathway

Author:
Kidonakis, Marios; Mullaj, Anisa; Stratakis, Manolis
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15553-15557
ISSN:
1520-6904
Subject:
acetophenones; aldehydes; carbonyl compounds; chemical structure; dimerization; gold; nanogold; organic chemistry; titanium dioxide
Abstract:
... Aromatic aldehydes and acetophenones undergo silylative pinacol-type reductive dimerization in their reaction with silylborane pinB-SiMe₂Ph (pin: pinacolato) catalyzed by supported Au nanoparticles on TiO₂. It is proposed that after initial activation of silylborane by Au nanoparticles and addition to the carbonyl functionality of an aromatic aldehyde or ketone, an aryl silyloxy radical is generat ...
DOI:
10.1021/acs.joc.8b02675

10. Selective [5 + 1] and [5 + 2] Cycloaddition of Ynamides or Propargyl Esters with Benzo[d]isoxazoles via Gold Catalysis

Author:
Xu, Wei; Zhao, Jidong; Li, Xiangdong; Liu, Yuanhong
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15470-15485
ISSN:
1520-6904
Subject:
Lewis bases; catalytic activity; chemical structure; chemoselectivity; cycloaddition reactions; esters; organic chemistry
Abstract:
... Benzo[d]isoxazoles are found to act as novel nucleophiles to undergo gold-catalyzed [5 + 1] or [5 + 2] cycloaddition reactions with ynamides. The reaction provides a concise and chemoselective access to polysubstituted 2H-benzo[e][1,3]oxazines or benzo[f][1,4]oxazepines. In addition, benzo[d]isoxazoles can also react with gold-carbene intermediates derived from propargyl esters to afford [5 + 1] a ...
DOI:
10.1021/acs.joc.8b02935

11. Chiroptical Inversion of Europium(III) Complexes by Changing a Remote Stereogenic Center of a C₂-Symmetric Bispyrrolidinoindoline Manifold

Author:
Taniguchi, Tomoaki; Tsubouchi, Akira; Imai, Yuki; Yuasa, Junpei; Oguri, Hiroki
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15284-15296
ISSN:
1520-6904
Subject:
chemical reactions; chemical structure; europium; ligands; luminescence; organic chemistry; pyridines
Abstract:
... As an effort to integrate natural products chemistry and coordination chemistry, a diastereomeric pair of chiral alkaloidal manifolds composed of a bispyrrolidinoindoline (BPI) framework was designed and synthesized to generate luminescent Euᴵᴵᴵ complexes with switchable chiroptical properties. The C₂-symmetric alkaloidal manifolds were linked with bis(benzimidazolyl)pyridine (BBIPy) as an achiral ...
DOI:
10.1021/acs.joc.8b02550

12. Nickel Catalyzed syn-Selective Aryl Nickelation and Cyclization of Aldehyde/Enone-Tethered Terminal Alkynes with Arylboronic Acids

Author:
Rajesh, Manda; Singam, Maneesh Kumar Reddy; Puri, Surendra; Balasubramanian, Sridhar; Sridhar Reddy, Maddi
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15361-15371
ISSN:
1520-6904
Subject:
Lewis bases; acids; alkynes; chemical reactions; chemical structure; nickel; organic chemistry
Abstract:
... A syn-arylative nickelation followed by nucleophilic syn-selective cyclization of o-propargyloxy benzaldehydes is achieved toward the synthesis of chromanol skeletons with alkenyl substitution at C3. The capture of the intermediate vinyl nickel in its cis geometry is done also with a Michael acceptor to synthesize 4-alkylated derivatives. This protocol is equally applicable to o-propargylamino ben ...
DOI:
10.1021/acs.joc.8b02618

13. Reactivity of Anodically Generated 4-Methoxystilbene Cation Radicals: The Influence of Ortho-Substituted Hydroxymethyl, Aminomethyl, and Carboxylic Acid Groups

Author:
Chong, Kam-Weng; Thomas, Noel F.; Low, Yun-Yee; Kam, Toh-Seok
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15087-15100
ISSN:
1520-6904
Subject:
Lewis bases; carboxylic acids; cations; chemical reactions; chemical structure; free radicals; organic chemistry; stilbenes
Abstract:
... The effect of ortho′-substituted side chains bearing nucleophilic groups such as CH₂OH, CH₂NHR, and CO₂H on the reactivity of anodically generated 4-methoxy- and 3,4-dimethoxystilbene cation radicals was investigated, and results were compared with those of substrates where the nucleophilic groups such as OH and NHR are directly attached to the aromatic ring. It was found that when ortho′-substitu ...
DOI:
10.1021/acs.joc.8b02360

14. [1]Benzothiophene-Fused Chiral Spiro Polycyclic Aromatic Compounds: Optical Resolution, Functionalization, and Optical Properties

Author:
Takase, Ko; Noguchi, Keiichi; Nakano, Koji
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15057-15065
ISSN:
1520-6904
Subject:
X-radiation; aromatic compounds; chemical reactions; enantiomers; fluorescence; high performance liquid chromatography; optical properties; organic chemistry; polycyclic compounds
Abstract:
... Spiro polycyclic aromatic compounds have been known as rigid chiral scaffolds. In order to extend their applications, an efficient preparation route to enantiopure derivatives is highly required. Here, we design 10,10′-spirobi[indeno[1,2-b][1]benzothiophene]-7,7′-diol to achieve efficient optical resolution. The compound was successfully synthesized and resolved by chiral HPLC on a semipreparative ...
DOI:
10.1021/acs.joc.8b02301

15. Enantioselective Total Synthesis and Assignment of the Absolute Configuration of the Furo[3,2-a]carbazole Alkaloid Furoclausine-B

Author:
Spindler, Benedikt; Kataeva, Olga; Knölker, Hans-Joachim
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15136-15143
ISSN:
1520-6904
Subject:
alkaloids; chemical bonding; enantioselectivity; epoxidation reactions; moieties; organic chemistry; palladium
Abstract:
... We describe the first enantioselective total synthesis and the assignment of the absolute configuration of the furo[3,2-a]carbazole alkaloid furoclausine-B. As key steps for our approach we used a palladium(II)-catalyzed double C–H-bond activation for the construction of the carbazole framework, a Shi epoxidation, and an intramolecular opening of the epoxide for annulation of the dihydrofuran moie ...
DOI:
10.1021/acs.joc.8b02426

16. Formal Total Synthesis of Hybocarpone Enabled by Visible-Light-Promoted Benzannulation

Author:
Chen, Wei; Guo, Renyu; Yang, Zhen; Gong, Jianxian
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15524-15532
ISSN:
1520-6904
Subject:
chemical structure; dimerization; organic chemistry; quinones
Abstract:
... The formal total synthesis of hybocarpone was achieved in eight steps from commercially available 1,2,4-trimethoxybenzene. Key transformations include a visible-light-promoted benzannulation to construct the key α-naphthol intermediate and a modified CAN-mediated dimerization/hydration cascade sequence to generate the vicinal all-carbon quaternary centers in a stereocontrolled manner. The total sy ...
DOI:
10.1021/acs.joc.8b02595

17. Synthesis of (±)-Naphthacemycin A₉

Author:
Wang, Shuai; Kraus, George A.
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15549-15552
ISSN:
1520-6904
Subject:
chemical reactions; chemical structure; organic chemistry; organic compounds
Abstract:
... Naphthacemycin A₉ was synthesized in nine steps by a sequence featuring a Diels–Alder reaction of a hindered aryl butadiene and a Hauser–Kraus annulation reaction. ...
DOI:
10.1021/acs.joc.8b02658

18. Tunable Copper-Catalyzed Reaction of C₆₀ with 2-Ethoxycarbonylacetamides and Subsequent BF₃·Et₂O-Mediated Isomerization of the Generated Dihydrofuran-Fused Fullerenes to Fulleropyrrolidinones

Author:
Teng, Qiaoqiao; Tan, Yi-Chen; Miao, Chun-Bao; Sun, Xiao-Qiang; Yang, Hai-Tao
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15268-15276
ISSN:
1520-6904
Subject:
air; chemical structure; fullerene; isomerization; organic chemistry; organic compounds; oxidants
Abstract:
... A tunable copper-catalyzed reaction of C₆₀ with 2-ethoxycarbonylacetamides using air as the oxidant has been explored, which selectively affords methanofullerenes (2) and dihydrofuran-fused fullerenes (3) under the CuI/DMAP and CuCl/NMI catalytic systems, respectively. Furthermore, the generated dihydrofuran-fused fullerenes could be transformed to fulleropyrrolidinones (4 and 5) upon treatment wi ...
DOI:
10.1021/acs.joc.8b02547

19. Synthesis of Functionalized Chromene and Chroman Derivatives via Cesium Carbonate Promoted Formal [4 + 2] Annulation of 2′-Hydroxychalcones with Allenoates

Author:
Rouh, Hossein; Liu, Yangxue; Katakam, Nandakumar; Pham, Lilian; Zhu, Yi-Long; Li, Guigen
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15372-15379
ISSN:
1520-6904
Subject:
ambient temperature; carbonates; cesium; chemical reactions; chemical structure; chemoselectivity; organic chemistry; organic compounds
Abstract:
... A new strategy has been established for the synthesis of functionalized chromene and chroman derivatives via a Cs₂CO₃-catalyzed domino addition of 2′-hydroxychalcone derivatives with allenoates, which can serve as a general avenue for the construction of multireplaced chromene derivatives. Chemoselectivity of this synthesis was found to depend on substituents on substrates. Good to excellent yield ...
DOI:
10.1021/acs.joc.8b02627

20. Atomic Charges

Author:
Wiberg, Kenneth B.; Rablen, Paul R.
Source:
Journal of organic chemistry 2018 v.83 no.24 pp. 15463-15469
ISSN:
1520-6904
Subject:
acidity; chemical reactions; chemical structure; energy; gases; hydrogen; hydrogen bonding; methanol; models; organic chemistry
Abstract:
... The problem of deriving atomic charges from the results of ab Initio MO calculations has been studied by the use of several reported methods: Mulliken population analysis, the minimal basis set (MBS) procedure, the natural population analysis (NPA), two electrostatic potential fitting methods, M-K and ChelpG, the Hirshfeld population analysis, and CM5 (charge model 5), which is related to the Hirs ...
DOI:
10.1021/acs.joc.8b02740