Two Propanediurea-based Cucurbituril Analogues: Bis-ns-TD[8] and NH-ns-TD[4]

Synlett ◽  
2018 ◽  
Vol 29 (18) ◽  
pp. 2381-2384
Author(s):  
Qiaochun Wang ◽  
Chunhua Dai ◽  
Yenan Shen
Keyword(s):  
Mass Spectrometry ◽  
1H Nmr Spectroscopy ◽  
High Resolution Mass Spectrometry ◽  
The Other ◽  
Amine Group ◽  
X Ray Diffraction ◽  
Excellent Thermal Stability ◽  
X Ray ◽  
Secondary Amine Group ◽  
Resolution Mass

Two new cucurbituril members, one containing two equivalent cavities and the other having an active secondary amine group, were synthesized by condensation of propanediurea (2,4,6,8-tetraazabicyclo[3.3.1]nonane-3,7-dione) with formaldehyde. These two macrocycles exhibit excellent thermal stability, and their structures were confirmed by single-crystal X-ray diffraction, 1H NMR spectroscopy, and high-resolution mass spectrometry.

Improved Access to 1,8-Dichloro-10-(ethynyl)anthracene: A Useful Building Block for (Semi-)rigid Organic Frameworks

Synthesis ◽  
2018 ◽  
Vol 50 (10) ◽  
pp. 2009-2018
Author(s):  
Jan-Hendrik Lamm ◽  
Philipp Niermeier ◽  
Leif Körte ◽  
Beate Neumann ◽  
Hans-Georg Stammler ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Building Block ◽  
High Resolution Mass Spectrometry ◽  
Cross Coupling ◽  
Easy Access ◽  
Coupling Reactions ◽  
X Ray Diffraction ◽  
X Ray ◽  
Cross Coupling Reactions ◽  
Resolution Mass

An easy access to 1,8-dichloro-10-(ethynyl)anthracene is reported, which is widely applicable for building up rigid linkers between two 1,8-dichloroanthracene units. For this, 1,8-dichloroanthren-10(9H)-one was reacted with ethynylmagnesium bromide in the presence of CeCl3; the yield was 65%. This building block was used as a substrate in (cross-)coupling reactions and some examples of linked 1,8-dichloroanthracen-10-yls (e.g., 1,8-bis[(1,8-dichloroanthracen-10-yl)-ethynyl]naphthalene or 1,2-bis[(1,8-dichloroanthracen-10-yl)ethynyl]-benzene) were synthesized in good to moderate yields. Linked 1,8-dichloroanthracen-10-yl derivatives were also synthesized by cross-coupling reactions using 10-bromo-1,8-dichloroanthracene and doubly ethynyl-substituted substrates. Linkers between the 1,8-dichloroanthracene units were: butadiynediyl, dimethylsilyldiethynyl, octa-1,7-diyne-1,8-diyl, propane-1,3-diylbis(dimethylsilyl)diethynyl, benzene-1,2-diethynyl, naphthalene-1,8-diyldiethynyl, and anthracene-1,8-diyldiethynyl. The new anthracene compounds were characterized by NMR spectroscopy, high-resolution mass spectrometry, and, in part, by X-ray diffraction experiments.

Structural Identification of Products from the Chloromethylation of Salicylaldehyde

Synlett ◽  
2018 ◽  
Vol 30 (01) ◽  
pp. 44-48 ◽  
Author(s):  
Muhammad Bala ◽  
Ebrahim Kadwa ◽  
Holger Friedrich
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
High Resolution Mass Spectrometry ◽  
Structural Identification ◽  
Spectroscopic Techniques ◽  
X Ray Diffraction ◽  
X Ray ◽  
Multinuclear Nmr Spectroscopy ◽  
Ir Spectroscopic ◽  
Resolution Mass

In the functionalization of salicylaldehyde to give 5-(chloromethyl)salicylaldehyde, two byproducts [5-(hydroxymethyl)salicylaldehyde and 5,5′-methylenebis(salicylaldehyde)] were also isolated. ­Detailed characterizations and structural analyses of all three products by single-crystal X-ray diffraction, multinuclear NMR spectroscopy, high-resolution mass spectrometry, and IR spectroscopic techniques are presented and discussed. A strategy is presented for the preferential isolation of the two byproducts through column chromatography.

scholarly journals Synthesis and Molecular Structure of tert-Butyl 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate

2014 ◽  
Vol 2014 ◽  
pp. 1-6 ◽  
Author(s):  
Tetsuji Moriguchi ◽  
Suvratha Krishnamurthy ◽  
Toru Arai ◽  
Taisuke Matsumoto ◽  
Koji Araki ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Mass Spectrometry ◽  
High Resolution Mass Spectrometry ◽  
Amino Acid Ester ◽  
Piperidine Ring ◽  
Monoclinic Space Group ◽  
X Ray Diffraction ◽  
X Ray ◽  
H Nmr ◽  
Resolution Mass

The compound tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate was synthesized as a cyclic amino acid ester from the corresponding ethyl 2-amino-4-(2-oxiranyl)butanoate HCl salt via an intramolecular lactonization reaction and was characterized by using 1H NMR spectroscopy and high-resolution mass spectrometry. The product was then recrystallized from dichloromethane/diethyl ether and its structure was determined via single crystal X-ray diffraction analysis. The crystal was found to be of the monoclinic space group P21/c (no. 14) with a = 10.217(2) Å, b = 11.676(3) Å, c = 10.273(3) Å, β = 114.186(13)°, and Dcalc = 1.350 g/cm3 at 123 K. The compound has bicyclo[2.2.2]octane structure including a lactone moiety and a piperidine ring, and the two diastereomers of the molecules are present in a 1 : 1 ratio in the crystal.

scholarly journals Synthesis of spiro[benzo[4,5]imidazo[2,1-b][1,3]thiazole-2,3-thiolane]s via sulfa-Michael/aldol cascade reactions

2019 ◽  
Vol 43 (1-2) ◽  
pp. 63-66 ◽  
Author(s):  
Jiaying Lei ◽  
Xinliang Fu ◽  
Yulin Huang ◽  
Xiaofang Li
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
High Resolution ◽  
High Resolution Mass Spectrometry ◽  
Cascade Reactions ◽  
Cascade Reaction ◽  
Crystallographic Analysis ◽  
X Ray ◽  
Resolution Mass

The sulfa-Michael/aldol cascade reaction of ( Z)-2-arylmethylidene-benzo[4,5]imidazo[2,1- b]thiazol-3(2H)-ones and 1,4-dithiane-2,5-diol afforded novel 2-aryl-4-hydroxy-spiro[benzo[4,5]imidazo[2,1- b][1,3]thiazole-2,3-thiolan]-3-ones in moderate yields. The structures of all the products were characterized thoroughly by nuclear magnetic resonance, infrared and high-resolution mass spectrometry together with X-ray crystallographic analysis.

scholarly journals Synthesis of Trithia-Borinane Complexes Stabilized in Diruthenium Core: [(Cp*Ru)2(η1-S)(η1-CS){(CH2)2S3BR}] (R = H or SMe)

Inorganics ◽  
2019 ◽  
Vol 7 (2) ◽  
pp. 21 ◽  
Author(s):  
Koushik Saha ◽  
Urminder Kaur ◽  
Rosmita Borthakur ◽  
Sundargopal Ghosh
Keyword(s):  
Mass Spectrometry ◽  
1H Nmr Spectroscopy ◽  
Chair Conformation ◽  
Membered Ring ◽  
Molecular Structures ◽  
Boat Conformation ◽  
X Ray Diffraction ◽  
X Ray ◽  
Butterfly Cluster ◽  
Tellurium Powder

The thermolysis of arachno-1 [(Cp*Ru)2(B3H8)(CS2H)] in the presence of tellurium powder yielded a series of ruthenium trithia-borinane complexes: [(Cp*Ru)2(η1-S)(η1-CS){(CH2)2S3BH}] 2, [(Cp*Ru)2(η1-S)(η1-CS){(CH2)2S3B(SMe)}] 3, and [(Cp*Ru)2(η1-S)(η1-CS){(CH2)2S3BH}] 4. Compounds 2–4 were considered as ruthenium trithia-borinane complexes, where the central six-membered ring {C2BS3} adopted a boat conformation. Compounds 2–4 were similar to our recently reported ruthenium diborinane complex [(Cp*Ru){(η2-SCHS)CH2S2(BH2)2}]. Unlike diborinane, where the central six-membered ring {CB2S3} adopted a chair conformation, compounds 2–4 adopted a boat conformation. In an attempt to convert arachno-1 into a closo or nido cluster, we pyrolyzed it in toluene. Interestingly, the reaction led to the isolation of a capped butterfly cluster, [(Cp*Ru)2(B3H5)(CS2H2)] 5. All the compounds were characterized by 1H, 11B{1H}, and 13C{1H} NMR spectroscopy and mass spectrometry. The molecular structures of complexes 2, 3, and 5 were also determined by single-crystal X-ray diffraction analysis.

Absolute stereochemistry of calopiptin

1968 ◽  
Vol 21 (8) ◽  
pp. 2095 ◽  
Author(s):  
JB Mc Alpine ◽  
NV Riggs ◽  
PG Gordon
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
High Resolution Mass Spectrometry ◽  
The Other ◽  
Methyl Groups ◽  
Lower Field ◽  
Methyl Group ◽  
Low Field ◽  
Absolute Stereochemistry ◽  
Resolution Mass

The α,α?-diaryl-β,β-dimethyltetrahydrofurenoid lignan, calopiptin, from Piptocalyx moorei has been converted by demethylenation and methylation into veraguensin, now also isolated from Trimenia papuana (both species, family Trimeniaceae). Ozonolysis yields (-)-2,3-dimethylsuocinic acid which establishes the absolute trans configuration of the methyl groups. The benzylic proton giving a signal at low field from the other in the p.m.r, spectrum is assigned as trans to the adjacent methyl group by shielding and spin-decoupling arguments. The signal moves to even lower field on nitration of one of the aryl groups, identified as 3,4-dimethoxyphenyl by competitive nitration experiments and high-resolution mass spectrometry. Calopiptin is 2R-(3,4-dimethoxyphenyl)-3S,4S-dimethyl-5S-(3,4-methylenedioxyphenyl)tetrahydrofuran.

scholarly journals Synthesis and Crystal Structure of Unexpected (1S,4R,5R,6S)-4-Cyano-2,2,6-trimethyl-3-azabicyclo[3.3.1]nonan-6-yl Acetate

2017 ◽  
Vol 70 (12) ◽  
pp. 1269
Author(s):  
Steven Gareth Williams ◽  
Mohan Bhadbhade ◽  
Roger Bishop ◽  
Alison Thavary Ung
Keyword(s):  
Crystal Structure ◽  
Mass Spectrometry ◽  
High Resolution Mass Spectrometry ◽  
Unit Cell Parameters ◽  
Synthesis And Crystal Structure ◽  
X Ray ◽  
Cell Parameters ◽  
X Ray Crystallography ◽  
Ir And Nmr Spectroscopy ◽  
Resolution Mass

The reaction of (–)-β-pinene with KCN under a mild bridged Ritter reaction gave (1S,5R,6S)-2,2,6-trimethyl-3-aza-bicyclo[3.3.1]non-3-en-6-yl acetate that subsequently reacted to provide an unexpected (1S,4R,5R,6S)-4-cyano-2,2,6-trimethyl-3-azabicyclo[3.3.1]nonane-6-yl acetate. The structure of the compound was determined by high-resolution mass spectrometry, and IR and NMR spectroscopy and confirmed by single crystal X-ray crystallography. The compound crystallises in the monoclinic P21 space group, with unit cell parameters a 8.6120 (17), b 7.4570 (15), c 11.189 (2) Å, and β 110.16 (3)°.

scholarly journals One-pot synthesis and the structure study of a new indoline spiropyran with cationic substituent

2019 ◽  
Vol 488 (5) ◽  
pp. 498-503
Author(s):  
A. D. Pugachev ◽  
A. S. Kozlenko ◽  
M. B. Lukyanova ◽  
B. S. Lukyanov ◽  
V. V. Tkachev ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
High Resolution ◽  
Single Crystals ◽  
High Resolution Mass Spectrometry ◽  
Structure Study ◽  
One Pot ◽  
X Ray ◽  
One Pot Synthesis ◽  
High Resolution Mass ◽  
Resolution Mass

One-pot synthesis and the structure study of a new salt spiropyran of indoline series containing 2H-chromenic vinyl-3H-indolium fragment as a substituent at the position 8 are described. The structure was confirmed by the method of NMR 1H and 13C spectroscopy, IR and high-resolution mass spectrometry. The single crystals of the compound were investigated by X-ray analysis. The structure was compared with the previously known isostructural analogue [10].

Synthesis of 1,2,3-triazole-substituted 6,7-dihydroindolizin-8(5H)-one derivatives mediated by Selectfluor

2019 ◽  
Vol 43 (5-6) ◽  
pp. 179-183
Author(s):  
Yulin Huang ◽  
Jiaying Lei ◽  
Xinliang Fu ◽  
Wenlin Xie ◽  
Xiaofang Li
Keyword(s):  
Mass Spectrometry ◽  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
High Resolution ◽  
High Resolution Mass Spectrometry ◽  
Crystallographic Analysis ◽  
X Ray ◽  
High Resolution Mass ◽  
Moderate Yield ◽  
Resolution Mass

The 1,2,3-triazole and 1 H-1,2,3-benzotriazole-substituted 6,7-dihydroindolizin-8(5 H)-one derivatives were synthesized by the reaction of ( E)-7-(arylmethylidene)-6,7-dihydroindolizin-8(5 H)-ones with 1,2,3-triazole and 1 H-1,2,3-benzotriazole in the presence of Selectfluor in moderate yield. The structures of all the products were characterized thoroughly by nuclear magnetic resonance, infrared, and high-resolution mass spectrometry together with X-ray crystallographic analysis.

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