4-(4’-methoxyphenyl)-3-buten-2-one

4-(4’-methoxyphenyl)-3-buten-2-one

cosy of4-(4’-methoxyphenyl)-3-buten-2-one


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(S)-2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrobenzo[e]pyrazino[1,2-a][1,4]diazepine-6,12(11H,12aH)-dione—Synthesis and Crystallographic Studies

Synthesis of the (S)-2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrobenzo[e]pyrazino[1,2-a][1,4]diazepine-6,12(11H,12aH)-dione (4)

(S)-piperazine-2-carboxylic acid dihydrochloride (5, 700 mg, 3.45 mmol, 1 equiv.) was dispersed in 50 mL of 1:1 water:dioxane mixture and treated with sodium hydroxide (276 mg, 6.89 mmol, 2 equiv.). After dissolution of the starting material, 4-chlorobenzoyl chloride (6, 0.49 mL, 3.79 mmol, 1.1 equiv.) was added and reaction mixture was stirred in room temperature for 18 h. The next day, the disappearance of starting material and formation of (S)-4-(4-chlorobenzoyl)piperazine-2-carboxylic acid (7) was confirmed by LRMS-ESI spectra. Then, isatoic anhydride (8, 1.69 g, 10.34 mmol, 3 equiv.) was added, followed by addition of sodium carbonate (1.10 g, 10.34 mmol, 3 equiv.); the reaction mixture was heated in 60 °C for 18 h. The following day, formation of the (S)-1-(2-aminobenzoyl)-4-(4-chlorobenzoyl)piperazine-2-carboxylic acid 9 was confirmed by LRMS-ESI spectra. The volatiles were evaporated under reduced pressure, then the residue was co-evaporated with toluene (3 × 50 mL) and dissolved in dry DMF. For cyclization of 9, HATU (3.93 g, 10.34 mmol, 3 equiv.) and DIPEA (1.80 mL, 10.34 mmol, 3 equiv.) were added, and reaction mixture was stirred in room temperature for 18 h. The day after, the volatiles were evaporated under reduced pressure and residue was dissolved in water:ethyl acetate biphasic system. The organic phase was washed with water (2 × 50 mL), 0.5 M HCl (3 × 50 mL), saturated sodium bicarbonate (1 × 50 mL), and dried over magnesium sulphate. The crude product dissolved in ethyl acetate was evaporated with silica gel (2 g) and purified by column chromatography using hexane:ethyl acetate 2:8 v/v mixture, followed by pure ethyl acetate. Yield: 711 mg (56%). 1H-NMR (500 MHz, DMSO-d6): 10.55, 10.45 (2 × s, 2 × NH); 7.80–7.70 (m, 1H, HAr); 7.70–7.40 (m, 5H, HAr); 7.30–7.20 (m, 1H, HAr); 7.20–7.00 (m, 1H, HAr); 4.45–3.30 (m, 7H, 3 × CH2, 1 × CH); 13C-NMR (125 MHz, DMSO-d6): 170.5, 169.5, 166.6, 136.6, 135.0, 134.2, 132.3, 130.9, 129.3, 129.0, 128.5, 128.3, 125.6, 124.0, 120.9, 51.7, 42.7, 42.2, 38.2; HRMS (ESI): m/z [M + H]+ calcd. for C19H17ClN3O3: 370.09530, 372.09235, found: 370.09517, 372.09206; m.p. 248–250 °C. [α]20D$$ = +290 (c 1.0, DMSO). IR (KBr): cm−1 3465, 3369, 3229, 3160, 3109, 3068, 2909, 2866, 1694, 1657, 1620, 1521, 1477, 1431, 1407, 1339, 1303, 1262, 1219, 1181, 1162, 1092, 1035, 1010.

Molbank 2017, 2017(4), M964; doi: 10.3390/M964

Communication

(S)-2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrobenzo[e]pyrazino[1,2-a][1,4]diazepine-6,12(11H,12aH)-dione—Synthesis and Crystallographic Studies

Adam Mieczkowski 1,*, Damian Trzybiński 2, Marcin Wilczek 3, Mateusz Psurski 4, Maciej Bagiński 1,3, Bartosz Bieszczad 1,3, Magdalena Mroczkowska 1,3 and Krzysztof Woźniak 2

1

Institute of Biochemistry and Biophysics Polish Academy of Sciences, Pawinskiego 5a, 02-106 Warsaw, Poland

2

Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, 02-089 Warsaw, Poland

3

Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland

4

Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, 12 R. Weigl, 53-114 Wroclaw, Poland

*

Correspondence: Tel.: +48-22-592-35-06; Fax: +48-22-592-21-90

Received: 12 October 2017 / Accepted: 25 October 2017 / Published: 27 October 2017

Abstract

: 

(S)-2-(4-Chlorobenzoyl)-1,2,3,4-tetrahydrobenzo[e]pyrazino[1,2-a][1,4]diazepine-6,12(11H,12aH)-dione was obtained in a three-step, one-pot synthesis, starting from optically pure (S)-2-piperazine carboxylic acid dihydrochloride. Selective acylation of the β-nitrogen atom followed by condensation with isatoic anhydride and cyclization with HATU/DIPEA to a seven-member benzodiazepine ring, led to the tricyclic benzodiazepine derivative. Crystallographic studies and initial biological screening were performed for the title compound.

Keywords:

 (S)-2-piperazinecarboxylic acid; tricyclic benzodiazepines; isatoic anhydride; cytotoxicity

http://www.mdpi.com/1422-8599/2017/4/M964/htm
file:///C:/Users/Inspiron/Downloads/molbank-2017-M964-s002.pdf


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Ethyl-2-butenoate

Abstract

For the last fifty years nuclear magnetic resonance spectroscopy, generally referred as NMR, is one of the most versatile techniques for elucidation of structure of organic compounds. Among all available spectrometric methods, NMR is the only technique which offers a complete analysis and interpretation of the entire spectrum. Due to improved experimental technology and novel approaches, over the last decade nuclear magnetic resonance (NMR) has shown a tremendous progress. Generally, NMR spectroscopy makes use of three approaches; those are one dimension (1D), two dimensions (2D) and three dimensions (3D). Usually, the first approach of 1D-NMR (1H DEPT, 13C, 15N, 19F, 31P, etc.) generates good information about the structure of simple organic compounds, but in case of larger molecules the 1D-NMR spectra are generally overcrowded. Hence, the second approach of 2D-NMR (COSY, DQFCOSY, MQFCOSY, HETCOR, HSQC, HMQC, HMBC, TOCSY, NOESY, EXSY, etc.) is used for the further larger molecules, but 2D-NMR spectra also becomes complex and overlapping when used for further very large molecules like proteins. Hence, so as to achieve high resolution and reduced overlapping in spectra of very large molecules, Multi Dimensional-NMR (Homonuclear and Heteronuclear) are generally used. This paper supports interpretation of structure of different organic compounds by different NMR techniques.

13C-NMR proton decoupled spectrum of Ethyl-2-butenoate in CDCl3.



DEPT spectrum of Ethyl-2-butenoate.




COSY







https://www.omicsonline.org/structural-elucidation-of-small-organic-molecules-by-1d-2d-and-multi-dimensional-solution-nmr-spectroscopy-2155-9872.S11-001.php?aid=12051&view=mobile
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Structural Elucidation of Small Organic Molecules by 1D, 2D and Multi Dimensional-Solution NMR Spectroscopy

Neeraj Kumar Fuloria* and Shivkanya Fuloria

Anuradha College of Pharmacy, Amravati University, Maharashtra, India

*Corresponding Author:

Dr. Neeraj Kumar Fuloria 
M.Pharm (Pharmaceutical Chemistry)
Head, M.Pharm (Quality Assurance)
Anuradha College of Pharmacy
Chikhli, Buldhana, Maharashtra, India
Tel: 8805680423
E-mail: nfuloria@gmail.com, nfuloria@rediffmail.com

Received date: January 10, 2013; Accepted date: January 30, 2013; Published date: February 07, 2013

Citation: Fuloria NK, Fuloria S (2013) Structural Elucidation of Small Organic Molecules by 1D, 2D and Multi Dimensional-Solution NMR Spectroscopy. J Anal Bioanal Tech S11:001. doi: 10.4172/2155-9872.S11-001

Copyright: © 2013 de Francisco TMG, et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

13C NMR OF PHENYL PROPIONATE

The NMR Spectrum of Iodoethane CH3CH2I

The CH₃ protons produce a peak at δ 1.8 but, instead of a single peak, a triplet is produced. This is because the CH₃ protons couple with the adjacent two CH₂ protons.

The CH₂ protons produce a peak at δ 3.2 but, instead of a single peak, a quartet is produced. This is because the CH₂ protons couple with the adjacent three CH₃protons.

In general, if there are 'n' protons three bonds away from the resonating group, the absorption will be split into a multiplet of n+1 lines.

2-propen-1-ol

HR-MAS NMR Spectroscopy in Material Science

Schematic of a HR-MAS stator with a magic angle gradient along the rotor spinning axis. 

The gradient 2D 1 H HR-MAS NMR COSY spectrum for the ionic liquid [MBPyrr] + [TFSI] - 







The 1 H HR-MAS NMR of the ionic liquid [MBPyrr] + TFSI - at 298K as a A) neat liquid and B)







Pictorial representation of the gradient produced along the magic angle of the rotor. B) The decay of two different water signals found in a 1N methanol solution of an AEM membrane with increasing gradient strength. Gradient strength values (G/cm) are shown above the stack plot. 







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