scholarly journals One-Pot Preparation of (NH)-Phenanthridinones and Amide-Functionalized [7]Helicene-like Molecules from Biaryl Dicar-boxylic Acids

Author(s):  
Takumi Furuta ◽  
Takuya Murai ◽  
Yongning Xing ◽  
Mayu Kurokawa ◽  
Toshifumi Kuribayashi ◽  
...  

A one-pot transformation of biaryl dicarboxylic acids to (NH)-phenanthridinone derivatives based on a Curtius rearrangement and subsequent basic hydrolysis was developed. This method is also applicable for the preparation of optically active amide-functionalized [7]helicene-like molecules. Furthermore, aza[5]helicene derivatives with a phosphate moiety were isolated as a product of the Curtius rearrangement step in the case of substrates that bear chalcogen atoms. The stereostructures of these products, revealed by X-ray diffraction analysis, suggested that chalcogen-bonding and pnictogen-bonding interactions might contribute to their stabilization. The configurational stability of the helicene-like molecules and their chiroptical properties were further investigated.

1987 ◽  
Vol 99 ◽  
Author(s):  
R. S. Liu ◽  
G. C. Lin ◽  
H. M. Sung ◽  
Y. C. Chen ◽  
O. C. C. Lin

ABSTRACTLa-Ba-Cu-O and Y-Ba-Cu-O superconducting systems have been successfully prepared by gel techniques with high degree of chemical homogeneity. The precursor gel was synthesized from mixture of the corresponding metallic nitrates and di-carboxylic acids. The sintered oxides prepared from the different dicarboxylic acids were all Tc = 90K perovskite superconductors. However differences in electrical and magnetic properties were also observed. Effects due to the different acids elucidated by magnetic susceptibility measurements and X-ray diffraction analysis will be discussed.


CrystEngComm ◽  
2021 ◽  
Author(s):  
Ying Wang ◽  
Yao-mei Fu ◽  
Si-qi You ◽  
xuexin Li ◽  
Xinlong Wang ◽  
...  

Two new zirconium−based heterometal−organic frameworks, Zr3CP3−Mn (1) and Zr3CP3−Ni (2) constructed from [Cp3Zr3(μ3−O)(μ2−OH)3(IN)3] secondary building units and transition metal cations, were successfully synthesized through one−pot method. Single-crystal X-ray diffraction analysis...


1995 ◽  
Vol 7 (2) ◽  
pp. 149-156
Author(s):  
Atsushi Morikawa ◽  
Masa-Aki Kakimoto ◽  
Yoshio Imai

Chiral phenylindanediamnine (+)-2 was synthesized starting from chiral phenyl-indanedicarboxylic acid by a Schmidt rearrangement. Ordered amine-acid AB-type monomers, 8 and 9, were also prepared by a controlled reaction of (+)-2 with diacid chlorides. Disordered and ordered polyamides were synthesized by the reaction of (+)-2 with dicarboxylic acids, and the self-condensation of 8 and 9, respectively. Both the ordered and disordered polyamides were soluble in various solvents. The polyamides composed of the same dicarboxylic acid prepared by the different routes showed the same circular dichroism spectra. X-ray diffraction of the polyamide films indicated that all of the polyamides were amorphous. The glass transition and decomposition temperatures ranged from 170 to 340°C and from 320 to 400 °C, respectively. Additionally, polyamides containing the same diacids displayed nearly equivalent physical properties.


Synlett ◽  
2017 ◽  
Vol 28 (17) ◽  
pp. 2262-2266 ◽  
Author(s):  
Ashutosh Bedekar ◽  
Blessy Rajan

An efficient protocol for the synthesis of unsymmetrical aza[7]helicenes has been developed. The bis-styryl-type substrates for regiospecific photodehydrogenative oxidative double cyclization to give helicenes were prepared by a one-pot Wittig–Heck sequence as well as a stepwise procedure. The derivatives were characterized by single-crystal X-ray diffraction analysis and fluorescence spectroscopy.


Synthesis ◽  
2019 ◽  
Vol 51 (17) ◽  
pp. 3345-3355 ◽  
Author(s):  
Fangchong Yuan ◽  
Wenwen Duan ◽  
Zeyu Li ◽  
Xi Luo ◽  
Min Zhang ◽  
...  

Efficient and convenient one-pot, three-component reactions of pyrrolidone, aromatic aldehydes and 1-phenyl-3-trifluoromethyl-5-pyrazolone afforded highly functionalized trifluoromethylated pyrazol-4-ylpyrrole-2,5-dione derivatives in good yields. The effect of solvents on the reaction efficiency and yield was briefly investigated. The structures of products were determined by spectral methods and X-ray diffraction analysis. The latter showed that the products formed have a strong intramolecular hydrogen bond, which made them particularly stable and the corresponding annulated products were not obtained by treatment with dehydrating reagents.


Synthesis ◽  
2020 ◽  
Vol 52 (12) ◽  
pp. 1779-1794 ◽  
Author(s):  
Cheng-Chung Wang ◽  
Chieh-Kai Chan ◽  
Chien-Yu Lai

An efficient and eco-friendly synthetic route for Friedländer quinoline synthesis of polysubstituted quinolines is described. This green chemical method starts from various 2-aminobenzophenones and mono- or dicarbonyl synthons and uses reusable Nafion NR50 material as a solid catalyst in ethanol under microwave irradiation. The protocol has a high generality of functional groups and provides the desired quinolines in good to excellent yields. Some structures were confirmed by single-crystal X-ray diffraction analysis.


Molbank ◽  
10.3390/m1022 ◽  
2018 ◽  
Vol 2018 (4) ◽  
pp. M1022 ◽  
Author(s):  
Serhii Holota ◽  
Yaroslav Shylych ◽  
Halyna Derkach ◽  
Olexandr Karpenko ◽  
Andrzej Gzella ◽  
...  

4-(1H-[1,2,4]-Triazol-5-ylsulfanyl)-1,2-dihydropyrazol-3-one (4) was synthesized with a yield of 55% via ring-switching hydrazinolysis of 5-ethoxymethylidenethiazolo[3,2-b][1,2,4] triazol-6-one (3) in ethanol medium. The initial 1H-[1,2,4]-triazole-3-thiol (1) was modified via a two-step reaction: S-alkylation with chloroacetic acid under Williamson reaction conditions, and further one-pot cyclization–condensation with triethylorthoformate in the acetic anhydride medium, yielding compound 3. The structures of compounds 3 and 4 were confirmed by LC-MS, NMR spectra and a single X-ray diffraction analysis (for compound 4).


Synthesis ◽  
2020 ◽  
Vol 53 (02) ◽  
pp. 344-347
Author(s):  
Hiroko Yamada ◽  
Naoki Aratani ◽  
Peifeng Mei ◽  
Ryo Kurosaki ◽  
Akinobu Matsumoto

AbstractA 2,2′-tert-butyl-5,9-6′,8′-cyclooctameric pyrenylene ([8]CP) was synthesized by a one-pot Suzuki–Miyaura cross-coupling reaction from two kinds of bifunctionalized monomers, as a rare example of a cyclic octamer. The octameric molecular structure of [8]CP was revealed by single-crystal X-ray diffraction analysis.


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