Molbank 2013, 2013(2), M797; doi:10.3390/M797

Short Note

2-Chloro-7-methyl-3-({4-[(4-nitrophenoxy)methyl]-1H-1,2,3-triazol-1-yl}methyl)quinoline

Koduru Sri Shanthi Praveena ¹, Nandula Yadagiri Sreenivasa Murthy ² and Sarbani Pal ^1,* 

¹ MNR Degree & PG College, Kukatpally, Hyderabad-500085, A.P., India² Department of Chemistry, School of Engineering, Anurag Group of Institutions, Ranga Reddy District-501301, A.P., India

http://www.mdpi.com/1422-8599/2013/2/M797

file:///C:/Users/Inspiron/Downloads/molbank-2013-M797.pdf

The title compound, 2-chloro-7-methyl-3-({4-[(4-nitrophenoxy)methyl]-1H-1,2,3-triazol-1-yl}methyl)quinoline was synthesized in one pot. The structure of the compound was fully characterized by IR, 1H and 13C-NMR, mass spectral analysis and elemental analysis.

 

Description of the compound 2: Off white solid.

Yield: 1.54 g, 94%.

M.p.: 175–177 °C.

Rf: 0.39 (Chloroform:Ethyl acetate = 3:1).

IR υmax (KBr, cm−1): 3151, 3118, 2924, 2852, 1594, 1496.0, 1340, 1264, 1230, 1111.

Mass (ES): m/z 410 (M+1, 100%).

1H-NMR (CDCl3, 400 MHz): δ 8.20 (d, J = 9.3 Hz, 2H), 7.94 (s, 1H), 7.80 (s, 2H), 7.66 (d, 1H, J = 8.3 Hz),

7.42 (d, 1H, J = 8.3 Hz), 7.07 (d, 2H, J = 9.3 Hz), 5.82 (s, 2H), 5.32 (s, 2H), 2.57 (s, 3H).

13C-NMR (CDCl3, 100 MHz): δ 163.0, 148.9, 147.9, 142.7, 142.4, 141.9, 140.8, 138.8, 137.0, 130.2,

127.4, 125.9, 125.3, 123.5, 114.9, 62.4, 51.5, 27.5.

Elemental analysis found C, 58.46; H, 3.79; N, 17.38. Calc. for C20H16ClN5O3; C, 58.61; H, 3.94; Cl,

8.65; N, 17.09; O, 11.71. 

 

ANDHRA FOOD

Synthesis of 2-{[5-(diphenylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}-N-(pyrazin- 2-yl) acetamide

2-{[5-(diphenylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}-N-(pyrazin- 2-yl) acetamide

Molbank 2013, 2013(2), M800; doi:10.3390/M800

Short Note

2-{[5-(Diphenylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}-N-(pyrazin-2-yl)acetamide

Prakash S. Nayak ¹, Badiadka Narayana ^1,* , Seranthimata Samshuddin ¹ and Balladka Kunhanna Sarojini ²

¹ Department of Studies in Chemistry, Mangalore University, Mangalagangotri-574 199, Karnataka, India² Research Department of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574153, Karnataka, India

nbadiadka@yahoo.co.uk.

http://www.mdpi.com/1422-8599/2013/2/M800
file:///C:/Users/Inspiron/Downloads/molbank-2013-M800.pdf

S-Alkylation of 5-(diphenylmethyl)-1,3,4-oxadiazole-2(3H)-thione (3) by 2-chloro-N-(pyrazin-2-yl)acetamide (2) affords the title compound, 2-{[5-(diphenylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}-N-(pyrazin-2-yl)acetamide (4). The intermediate (2), in turn, was prepared by the acetylation of 2-aminopyrazine (1) with chloroacetyl chloride. The structure of the newly synthesized compound is characterized by IR, NMR and mass spectral data.

Melting point: 210–212 °C.
LCMS: m/z = 404.5 (M++1).

IR (KBr): νmax (cm−1), 3201 (N-H), 3041 (Ar-H), 1699 (alkyl-CO-NH) , 1555 (C=N, Ar C=C).
1H-NMR (400 MHz, DMSO-d6): δ ppm, 4.53 (s, 2H, S-CH2), 5.93 (s, 1H, Ph2-CH), 7.22–7.36 (m,
11H, Ar-H), 8.38–8.41 (m, 2H, Ar-H), 11.15 (s, 1H, NH).


13C-NMR (100 MHz, DMSO-d6,): δ ppm, 168.52 (C=O), 166.41, 163.89 (oxadiazole C’s), 148.75,
143.11, 140.54, 139.07, 136.55, 129.14, 128.75, 127.82 (aromatic C’s), 47.61(S-CH2), 36.78 (Ph2-CH).


Elemental analysis: Calculated for C21H17N5O2S, C, 62.52%; H, 4.25%; N, 17.36%; Found: C,
62.49%; H, 4.28%; N, 17.32%.

The formation of 2-{[5-(diphenylmethyl)-1,3,4-oxadiazol-2-yl]sulfanyl}-N-(pyrazin-2-yl)acetamide
(4) was confirmed by its NMR and mass spectral data. A singlet integrating for two protons at δ 4.53
in the 1H-NMR spectrum of compound (4) was due to -S-CH2 linkage. Another singlet observed at δ
5.93 ppm was due to the proton attached the carbon for which two phenyl groups were substituted. The signals of aromatic protons merged in the regions δ 7.22–7.36 ppm and 8.38–8.41 ppm as multiplets.NH proton appeared as a singlet at δ 11.15 ppm as a singlet. Mass spectrum showed a molecular ionpeak at m/z 404.5 (M++1) corresponding to the molecular formula of C21H17N5O2S. Elemental analysis and 13C-NMR spectrum also gave satisfactory results for the title compound.






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cock

1H NMR of the 2-Amino-4-phenyl-3-cyano-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline

¹H NMR of the 2-Amino-4-phenyl-3-cyano-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline 5a





http://article.sapub.org/10.5923.j.chemistry.20140401.04.html

American Journal of Chemistry

p-ISSN: 2165-8749    e-ISSN: 2165-8781

2014;  4(1): 29-34

doi:10.5923/j.chemistry.20140401.04

Harvinder Singh Sohal¹, Rajshree Khare¹, Arun Goyal¹, Andrew Woolley², Kishanpal Singh³, Rajeev Sharma⁴

¹Department of Chemistry, Maharishi Markandeshwar University, Mullana-133 207, Haryana, India

²Department of Chemistry, University of Toronto, 80 St. George St. Toronto, ON, M5S 3H6, Canada

³Department of Chemistry, Punjabi University, Patiala-147 001, Punjab, India

⁴Department of Chemistry, Multani Mal Modi College, Patiala-147 001, Punjab, India

Correspondence to: Harvinder Singh Sohal, Department of Chemistry, Maharishi Markandeshwar University, Mullana-133 207, Haryana, India.

Email:

Multi-component Approach for the Synthesis of Fused Dihydropyridines via Unsymmetrical Hantzch Condensation Using Glycerol as Green Solvent

2-Amino-4-phenyl-3-cyano-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline (5a): 

mp. 277–278 °C; IR (KBr): ΰ = 3436, 3324, 3214, 2197, 1719, 1498 cm⁻¹. 

¹H NMR (400 MHz, CDCl₃): δ(ppm) = 1.02 (s, 3H, CH₃), 1.09 (s, 3H, CH₃), 2.01–2.37 (m, 4H, 2×CH₂), 4.38 (s, 1H, CH), 5.36 (s, 2H, NH₂), 7.07–7.29 (m, 5H, ArH), 8.94 (s, 1H, NH). 


¹³C NMR (100 MHz, CDCl₃): δ(ppm) = 27.4, 29.5, 32.8, 36.9, 39.4, 50.8, 59.7, 113.5, 119.7, 126.2, 127.8, 128.4, 143.9, 155.3, 166.3, 197.7.

MS (EI) m/z 294.3 (M+). 

Anal. Calcd for C₁₈H₁₉N₃O: C, 73.72; H, 6.48; N, 14.33. Found: C, 73.61; H, 6.58; N, 14.31.


Maharishi Markandeshwar University, Mullana













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COSY , COSYDQF , Long-range COSY

COSY

This technique allows to observe a pulse spin-spin interaction constant of less than 1 Hz. 
This example shows the interaction of the aldehyde proton (17) and the protons of the methylene group (18,19) with the protons of the benzene ring.

LONG RANGE COSY






NOESY..........Correlation protons located close in space.






HXCORR

DOSY

Spectra allows to select individual compounds from mixtures, but only when a sufficient difference in the diffusion coefficients

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Nyköping (Sweden)-houses.

Fjallbacka, a colorful fishing Village along the west coast of Sweden

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Stockholm, Sweden

Sweden Stockholm

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Despite the cold weather, public came and enjoyed different activities. The famous chef, Paul Svensson who works in one of the fanciest and most famous …

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APT (Attached Proton Test)

APT (Attached Proton Test)

Analogue techniques DEPT, but unlike it allows us to observe signals of quaternary carbon atoms (a)

DEPT (Distortionless Enhancement by Polarization Transfer)

Allow to distinguish signals of quaternary carbon atoms, CH, CH 2 and CH 3 groups.

Experiment DEPT (Distortionless Enhancement by Polarization Transfer) allows to distinguish between signals of quaternary, methine, methylene and methyl carbon atoms in the range of 13 C.

Depending on the multiplicity of the signals may be either positive or negative intensity. The most commonly used kind of experiment is DEPT DEPT135, in which the signals of the methylene carbon atoms - have negative intensity, methine and methyl - positive, and the signals of carbon atoms not directly associated with the protons do not appear. The spectrum exhibited only signals DEPT90 methine carbons and the spectrum DEPT45 quaternary carbons are not shown, and other signals - positive.

Experiment DEPT, usually used in conjunction with experiment 13 C with complete suppression of the spin-spin coupling (13 C { 1 H} experiment). From the analysis of the spectra of 13 C with suppression, DEPT135 and DEPT90 possible to draw conclusions about the multiplicity of all carbon atoms in the molecule.

As a result of polarization transfer to protons on the carbon atoms in the DEPT experiment of the sensitivity of the method is approximately four times greater than that of the standard experimental 13 C to complete suppression, and the experiment APT (Attached Proton Test).

DEPT experiment is less critical to the accuracy of selecting the value of direct constants C-H used to calculate a delay in the pulse sequence than experiment INEPT. This feature is useful in analyzing the structure containing carbon atoms of different natures, CH constants which respectively vary widely.