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Showing posts with label nmr. Show all posts
Showing posts with label nmr. Show all posts

Monday, 13 November 2017

1,1'-(4'-(tert-butoxy)-4-(dimethylamino)-[1,1'-biphenyl]-2,6-diyl)diethanone

Image result for COCK ANIMATION

1,1'-(4'-(tert-butoxy)-4-(dimethylamino)-[1,1'-biphenyl]-2,6-diyl)diethanone

NMR IS EASY
Image result for MOM WILL TEACH NMR
MOM CAN TEACH















13C NMR PREDICT



CC(C)(C)Oc1ccc(cc1)c2c(cc(cc2C(C)=O)N(C)C)C(C)=O


Image result for MOM WILL TEACH NMR
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“ORG SPECT INT” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

Thursday, 9 November 2017

Transition-Metal-Free Cross-Coupling of Aryl and Heteroaryl Thiols with Arylzinc Reagents

Zhong-Xia WANG
STR1

STR1

N,N-dimethyl-4-biphenylamine

 
 
Molecular Formula, C14H15N
 
Molecular Weight, 197.28
 
CAS Number, 1137-79-7
(1) N,N-dimethyl-[1,1'-biphenyl]-4-amine (3a) 5,6
Elute: EtOAc/petroleum ether: 1/100 (v/v), white solid, yield 97.8 mg (99%).
1H NMR (400 MHz, CDCl3): δ 7.56 (d, J = 7.8 Hz, 2H), 7.51 (d, J = 8.8 Hz, 2H), 7.40 (t, J = 7.7 Hz, 2H), 7.30–7.21 (m, 1H), 6.81 (d, J = 8.8 Hz, 2H), 3.00 (s, 6H).
13C NMR (101 MHz, CDCl3): δ 150.09, 141.34, 129.37, 128.78, 127.84, 126.43, 126.12, 112.90, 40.97.
5 Yang, X.; Wang, Z.-X. Organometallics 2014, 33, 5863.
(6) Stibingerova, I.; Voltrova, S.; Kocova, S.; Lindale, M.; Srogl, J. Org. Lett. 2016, 18, 312.
STR1 STR2

Transition-Metal-Free Cross-Coupling of Aryl and Heteroaryl Thiols with Arylzinc Reagents

Bo Yang and Zhong-Xia Wang* 
 CAS Key Laboratory of Soft Matter Chemistry, Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China
 Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. China
Org. Lett., Article ASAP
DOI: 10.1021/acs.orglett.7b03145
 
*E-mail: zxwang@ustc.edu.cn.

Abstract

Abstract Image
Cross-coupling of (hetero)arylthiols with arylzinc reagents via C–S cleavage was performed under transition-metal-free conditions. The reaction displays a wide scope of substrates and high functional-group tolerance. Electron-rich and -deficient (hetero)arylthiols and arylzinc reagents can be employed in this transformation. Mg2+ and Li+ ions were demonstrated to facilitate the reaction.
In summary, we developed a transition-metal-free coupling reaction of (hetero)arylthiols with arylzinc reagents to form bi(hetero)aryls. The reaction exhibited wide substrate scope and good compatibility of functional groups. Electron-rich and -poor aryl or heteroaryl thiols can be converted. Various arylzinc reagents, including electron-rich and electron-poor reagents, can be employed as the coupling partners. Preliminary mechanistic studies suggest a nucleophilic aromatic substitution pathway, and Mg2+ and Li+ ions play important roles in the process of reaction. This study provides an example of S2– as a leaving group in an aromatic system and an effective methodology for the synthesis of bi(hetero)aryls including pharmaceutical molecules without transition-metal impurities.
Zhong-Xia WANG
   
Department:Department of Chemistry
Mailing Address:
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Rd, Hefei, Anhui, 230026, PR China
Postal Code:230026
Phone:+86-551-63603043
Fax: 
Homepage:http://chem.ustc.edu.cn/szdw_16/bd/201210/t20121023_142877.html
 
Zhong-Xia Wang is a professor in the Department of Chemistry at the University of Science and Technology 
of China. He received his BS degree (1983) and MS degree (1986) from Nankai University, 
and PhD degree (1997) from the University of Sussex, UK. Since July 1986, Wang has been working 
at the University of Science and Technology of China (USTC) successively as Assistant, 
Lecturer, Associate Professor, and Professor. From Aug. 1993 to Oct. 1996, he pursued his doctoral 
studies at the University of Sussex, UK, and from Oct. 1999 to Oct. 2000, he was a Research Associate 
at the Chinese University of Hong Kong.

 学 系
Department of Chemistry

Predicts
STR1
STR1

“ALL FOR DRUGS” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

Transition-Metal-Free Cross-Coupling of Aryl and Heteroaryl Thiols with Arylzinc Reagents

Zhong-Xia WANG
STR1

STR1

N,N-dimethyl-4-biphenylamine

 
 
Molecular Formula, C14H15N
 
Molecular Weight, 197.28
 
CAS Number, 1137-79-7
(1) N,N-dimethyl-[1,1'-biphenyl]-4-amine (3a) 5,6
Elute: EtOAc/petroleum ether: 1/100 (v/v), white solid, yield 97.8 mg (99%).
1H NMR (400 MHz, CDCl3): δ 7.56 (d, J = 7.8 Hz, 2H), 7.51 (d, J = 8.8 Hz, 2H), 7.40 (t, J = 7.7 Hz, 2H), 7.30–7.21 (m, 1H), 6.81 (d, J = 8.8 Hz, 2H), 3.00 (s, 6H).
13C NMR (101 MHz, CDCl3): δ 150.09, 141.34, 129.37, 128.78, 127.84, 126.43, 126.12, 112.90, 40.97.
5 Yang, X.; Wang, Z.-X. Organometallics 2014, 33, 5863.
(6) Stibingerova, I.; Voltrova, S.; Kocova, S.; Lindale, M.; Srogl, J. Org. Lett. 2016, 18, 312.
STR1 STR2

Transition-Metal-Free Cross-Coupling of Aryl and Heteroaryl Thiols with Arylzinc Reagents

Bo Yang and Zhong-Xia Wang* 
 CAS Key Laboratory of Soft Matter Chemistry, Hefei National Laboratory for Physical Sciences at Microscale and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China
 Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, P. R. China
Org. Lett., Article ASAP
DOI: 10.1021/acs.orglett.7b03145
 
*E-mail: zxwang@ustc.edu.cn.

Abstract

Abstract Image
Cross-coupling of (hetero)arylthiols with arylzinc reagents via C–S cleavage was performed under transition-metal-free conditions. The reaction displays a wide scope of substrates and high functional-group tolerance. Electron-rich and -deficient (hetero)arylthiols and arylzinc reagents can be employed in this transformation. Mg2+ and Li+ ions were demonstrated to facilitate the reaction.
In summary, we developed a transition-metal-free coupling reaction of (hetero)arylthiols with arylzinc reagents to form bi(hetero)aryls. The reaction exhibited wide substrate scope and good compatibility of functional groups. Electron-rich and -poor aryl or heteroaryl thiols can be converted. Various arylzinc reagents, including electron-rich and electron-poor reagents, can be employed as the coupling partners. Preliminary mechanistic studies suggest a nucleophilic aromatic substitution pathway, and Mg2+ and Li+ ions play important roles in the process of reaction. This study provides an example of S2– as a leaving group in an aromatic system and an effective methodology for the synthesis of bi(hetero)aryls including pharmaceutical molecules without transition-metal impurities.
Zhong-Xia WANG
   
Department:Department of Chemistry
Mailing Address:
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Rd, Hefei, Anhui, 230026, PR China
Postal Code:230026
Phone:+86-551-63603043
Fax: 
Homepage:http://chem.ustc.edu.cn/szdw_16/bd/201210/t20121023_142877.html
 
Zhong-Xia Wang is a professor in the Department of Chemistry at the University of Science and Technology 
of China. He received his BS degree (1983) and MS degree (1986) from Nankai University, 
and PhD degree (1997) from the University of Sussex, UK. Since July 1986, Wang has been working 
at the University of Science and Technology of China (USTC) successively as Assistant, 
Lecturer, Associate Professor, and Professor. From Aug. 1993 to Oct. 1996, he pursued his doctoral 
studies at the University of Sussex, UK, and from Oct. 1999 to Oct. 2000, he was a Research Associate 
at the Chinese University of Hong Kong.

 学 系
Department of Chemistry

Predicts
STR1
STR1

“ALL FOR DRUGS” CATERS TO EDUCATION GLOBALLY, No commercial exploits are done or advertisements added by me. This is a compilation for educational purposes only. P.S. : The views expressed are my personal and in no-way suggest the views of the professional body or the company that I represent

Wednesday, 8 November 2017

Metal-free synthesis of polysubstituted pyrroles using surfactants in aqueous medium


Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC01874F, Communication
Amrendra Kumar, Ramanand, Narender Tadigoppula
An efficient and metal-free method has been developed for the synthesis of polysubstituted pyrrole derivatives with combination of sodium dodecyl sulphate (SDS) and Triton X-100 surfactants using water as a solvent at room temperature in 2-6 h and under microwave conditions (10 min) with good to excellent yields.

Metal-free synthesis of polysubstituted pyrroles using surfactants in aqueous medium

 

Image result for Narender Tadigoppula

Dr. Narender Tadigoppula

Principal Scientist
Medicinal & Process Chemistry
Central Drug Research Institute
India
Dr. Narender Tadigoppula is currently principal scientist in the department of medicine chemistry central drug research institute. He published more than 30 research articles. His major major research activities are identification of biologically active lead molecules through activity guided fraction and isolation work on the medicinal plants, marine organisms and microorganisms for metabolic diseases (hyperglycemia, dyslipidemia), parasitic diseases (leishmania and malaria), cancer etc., and chemical transformation of natural products of biological importance to improve their potency. We synthesize these biologically active lead molecules and their analogues in our laboratory. We have identified several lead molecules from the Indian medicinal plants for various disease areas as described below and further work is in progress to develop natural products based drugs.

Abstract

An efficient and metal-free method has been developed for the synthesis of polysubstituted pyrrole derivatives via intermolecular cycloaddition of substituted 1-phenyl-2-(phenylamino)-ethan-1-one/1-phenyl-2-(phenylamino)-propan-1-ones/2-((4-methoxyphenyl)amino)-1-(thiophen-2-yl)ethan-1-one/1-(furan-2-yl)-2-((4-methoxyphenyl)amino)ethan-1-one/1-(benzofuran-3-yl)-2-((4-methoxyphenyl)amino)ethan-1-one and dialkyl acetylene dicarboxylate/ethylbutynoate in the presence of a combination of sodium dodecyl sulphate (SDS) and Triton X-100 surfactants using water as a solvent at room temperature in 2–6 h under microwave conditions (10 min) with good to excellent yields.
Diethyl-1-(4-methoxyphenyl)-4-(p-tolyl)-1H-pyrrole 2,3dicarboxylate
STR1
white solid, yield 77%, mp 128-130 ;
1H NMR (400 MHz, CDCl3) δ 7.38(d, J = 8.2,2H), 7.31 (d, J = 7.9, 2H), 7.21 (d, J = 7.12, 2H), 6.99-6.96 (m, 3H), 4.31 (q, J = 7.2 Hz, 2H), 4.12 (q, J = 7.6Hz, 2H), 3.88 (s, 3H), 2.38 (s, 3H), 1.31 (t, J = 7.9Hz, 3H), 1.19 (t, J = 7.5Hz, 3H) ;
13C NMR (100 MHz, CDCl3) δ 166.3, 159.9, 149.0, 148.8, 136.7, 132.6, 130.3, 129.2, 127.6, 125.8, 124.5, 123.4, 121.5, 118.3, 110.5, 110.2, 61.2, 60.7, 56.0, 21.1, 14.0, 13.9.
IR (KBr) ṽ (cm-1): 2981.9, 1717.9, 1514.1, 1419.2, 1381.3, 1245.0, 1175.9, 1226.7, 1043.6, 835.7, 755.3, 663.
HRESIMS: m/zcalcd for [M+H]+ C24H26NO5 408.1805 found 408.1845.
STR1 STR2

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O=C(OCC)c2c(c(cn2c1ccc(OC)cc1)c3ccc(C)cc3)C(=O)OCC

tert-Butyl 4-(2,3-diaminophenyl)piperazine-1- carboxylate

str1
str2

tert-Butyl 4-(2,3-diaminophenyl)piperazine-1- carboxylate (4)
1H NMR (400 MHz, CDCl3), δ in ppm = 6.68 (t, 1H), 6.59 (d, J = 8.8 Hz, 1H), 6.55 (d, J = 7.6 Hz, 1H), 3.56 (br s, 8H), 2.83 (s, 4H), 1.49 (s, 9H). This is consistent with literature data.1

Small molecule piperazinyl-benzimidazole antagonists of the gonadotropin-releasing hormone (GnRH) receptor

 

Abstract

In this communication, we report the synthesis and characterization of a library of small molecule antagonists of the human gonadotropin releasing hormone receptor based upon the 2-(4-tert-butylphenyl)-4-piperazinyl-benzimidazole scaffold via Cu-catalysed azide alkyne cycloaddition. Our main purpose was to find a more soluble compound based on the WAY207024 lead with nanomolar potency to inhibit the GnRH receptor. A late stage diversification by the use of click chemistry was, furthermore developed to allow for expansion of the library in future optimisations. All compounds were tested in a functional assay to determine the individual potency of inhibiting stimulation of the receptor by the endogenous agonist GnRH. In conclusion, we found that compound 8ashowed improved solubility compared to WAY207024 and nanomolar affinity to GnRH receptor.
Graphical abstract: Small molecule piperazinyl-benzimidazole antagonists of the gonadotropin-releasing hormone (GnRH) receptor
//////////////
References 1. Pelletier, J. C.; Chengalvala, M.; Cottom, J.; Feingold, I.; Garrick, L.; Green, D.; Hauze, D.; Huselton, C.; Jetter, J.; Kao, W.; Kopf, G. S.; Lundquist, J. T. t.; Mann, C.; Mehlmann, J.; Rogers, J.; Shanno, L.; Wrobel, J., 2-phenyl-4-piperazinylbenzimidazoles: orally active inhibitors of the gonadotropin releasing hormone (GnRH) receptor. Bioorganic & medicinal chemistry 2008, 16 (13), 6617-40.

Sunday, 5 November 2017

Oxidant- and hydrogen acceptor-free palladium catalyzed dehydrogenative cyclization of acylhydrazones to substituted oxadiazoles



Org. Chem. Front., 2018, Advance Article
DOI: 10.1039/C7QO00749C, Research Article
Qiangqiang Jiang, Xinghui Qi, Chenyang Zhang, Xuan Ji, Jin Li, Renhua Liu
An efficient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles has been developed through palladium(0) catalyzed dehydrogenative cyclization of N-arylidenearoylhydrazides without oxidants and hydrogen acceptors.

Oxidant- and hydrogen acceptor-free palladium catalyzed dehydrogenative cyclization of acylhydrazones to substituted oxadiazoles


Abstract

An efficient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles has been developed through palladium(0) catalyzed dehydrogenative cyclization of N-arylidenearoylhydrazides. By using this method, a wide range of functionalized and potentially biologically relevant 1,3,4-oxadiazole-containing compounds have been accessed in moderate to high isolated yields. The dehydrogenative cyclization process is characterized by the nonuse of any sacrificing hydrogen acceptors or oxidants and hydrogen gas as the only by-product, and therefore circumvents the recurring problems of over-oxidation and the compatibility with easily oxidizable functionalities in oxidation protocols.

109.6 mg, 87 % yield; White solid,

1H NMR (400 MHz, CDCl3) δ 8.13 – 8.08 (m, 2H), 8.06 (d, J = 8.7 Hz, 2H), 7.52 (m, 3H), 7.01 (d, J = 8.7 Hz, 2H), 3.86 (s, 3H);

13C NMR (100 MHz, CDCl3) δ 164.51, 164.10, 162.33, 131.54, 129.03, 128.67, 126.80, 124.05, 116.38, 114.50, 55.46; M.p. 145-146 oC.

2-(4-methoxyphenyl)-5-phenyl-1,3,4-oxadiazole12


1H NMR CDCL3






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Saturday, 4 November 2017

Learn spectroscopy, Valeric acid or pentanoic acid. PROBLEM 1

.Image result for MOTHER TO TEACH NMR



HE IS EXCITED TOO



Product Name: Valeric acid


CAS:109-52-4




valeric acid

pentansäure

acide pentanoic

ペンタン酸

109-52-4 CAS

C5H10O2














Valeric acid, or pentanoic acid.


This 13C spectrum exhibits resonances at the following chemical shifts, and with the multiplicities indicated:


Shift (ppm)
Mult.
180.8
S
33.8
T
26.8
T
22.4
T
3.58
Q


(C5H10O2)



A= 13.4

B=22.4

C=26.8

D=33.8

E=180.6














1H NMR BELOW


t=0.78

m=1.22

m=1.46

t=2.2

s=11.8

















NMR IS EASY

EVEN MOM CAN TEACH YOU







2D [1H,1H]-TOCSY

Concentration: 100 mM

temperature: 298 K

pH: 7.4









1D DEPT90

Concentration: 100 mM

temperature: 298 K

pH: 7.4















1D DEPT135

Concentration: 100 mM

temperature: 298 K

pH: 7.4







2D [1H,13C]-HSQC

Concentration: 100 mM

temperature: 298 K

pH: 7.4










2D [1H,13C]-HMBC

Concentration: 100 mM

temperature: 298 K

pH: 7.4

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