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

Friday, 8 December 2017

Ruthenium-Catalyzed Tandem C–H Fluoromethylation/Cyclization of N-Alkylhydrazones with CBr3F: Access to 4-Fluoropyrazoles

Figure
4-Fluoropyrazoles are accessible in a single step from readily available aldehyde-derived N-alkylhydrazones through double C–H fluoroalkylation with tribromofluoromethane (CBr3F). RuCl2(PPh3)3 has been proven to be the most efficient catalyst for this transformation when compared to a range of other Cu-, Pd-, or Fe-based catalyst systems.
Image result for Didier Bouyssi
Univ Lyon, Université Claude Bernard Lyon 1, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS, CNRS UMR 5246), F-69622 Villeurbanne, France
J. Org. Chem.201782 (6), pp 3311–3316
DOI: 10.1021/acs.joc.7b00085
Ruthenium-Catalyzed Tandem C–H Fluoromethylation/Cyclization of N-Alkylhydrazones with CF3BR: Access to 4-Fluoropyrazoles

The importance of fluorine-containing pyrazoles to the pharmaceutical and agrochemical industries has been steadily increasing in recent years. As a consequence, the development of methods suitable for the incorporation of fluorine or fluoroalkyl groups into the pyrazole ring continues to be the subject of intense research.
Predicated on their previous copper-catalyzed synthesis of 4-substituted pyrazoles, Bouyssi, Monteiro and their co-worker from the Institut de Chemie et Biochemie Moléculaires et Supramoléculaires reported a ruthenium-catalyzed synthesis of substituted-4-fluoropyrazoles ( J. Org. Chem. 2017823311). The requisite starting materials, aldehyde derived N,N-dialkylhydrazones, were readily synthesized. Tribromofluoromethane served as the source of fluorine.
The commercially available and inexpensive ruthenium complex, RuCl2(PPh3)3, was discovered to be a very effective catalyst for this transformation. Diglyme was the preferred solvent for the reaction. The reaction displayed good tolerance for a variety of functional groups, including cyano, ester, formyl, and halide.
In general, higher yields were obtained with electron-withdrawing substituents. This novel methodology affords substituted-4-fluoropyrazoles in good yields in one step from readily available starting materials.

                                                 2K

3-(Benzo[d][1,3]dioxol-5-yl)-4-fluoro-1-methyl-1H-pyrazole (2k)
Chromatography using ethyl acetate/cyclohexane (gradient elution 30:70 to 50:50) gave the title compound as a pale yellow solid (79 mg, 60%).
Mp = 82–85 °C.
1H NMR (400 MHz, CDCl3) δ 7.35–7.31 (m, 2H), 7.27 (d, J = 4.8 Hz, 1H), 6.85 (d, J = 8.5 Hz, 1H), 5.97 (s, 2H), 3.83 (s, 3H).
13C NMR (101 MHz, CDCl3) δ 148.0, 147.2, 146.8 (d, J = 248.0 Hz), 136.7 (d, J = 6.2 Hz), 125.3 (d, J = 4.2 Hz), 119.8 (d, J = 4.7 Hz), 117.5 (d, J = 28.6 Hz), 108.6, 106.6 (d, J = 3.7 Hz), 101.1, 40.0 (s).
19F NMR (282 MHz, CDCl3) δ −178.2 (s). HRMS (ESI): Calcd for C11H10FN2O2 [M + H+]: 221.0721, found 221.0728.

Figure

alexis prieto

Alexis prieto

Chercheur postdoctoral chez Melchiorre group, ICIQ

Melchiorre group, ICIQ

Didier Bouyssi at Claude Bernard University Lyon 1
Univ Lyon, Université Claude Bernard Lyon 1, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS, CNRS UMR 5246), F-69622 Villeurbanne, France
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“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

Tuesday, 21 November 2017

2,4-dimorpholinocyclopent-2-enone


1465003-25-1 cas

2,4-dimorpholinocyclopent-2-enone (1b):
1H NMR (300 MHz, CDCl3) 6.24 (d, J = 2.9 Hz, 1H, COC=CH), 3.78 (t, J = 4.7 Hz, 4H, morpholine), 3.73 (t, J = 4.7 Hz, 4H, morpholine), 3.73-3.72 (m, 1H, COCH2CHN), 3.15-3.14 (m, 4H, morpholine), 2.54-2.52 (m, 4H, morpholine), 2.49-2.48 (m, 1H, COCH2), 2.46-2.45 (m, 1H, COCH2);
13C NMR (75 MHz, CDCl3) 38.1, 48.1, 50.0, 60.3, 66.6, 67.1, 129.5, 151.7, 202.0.

Water excellent solvent for the synthesis of bifunctionalized cyclopentenones from furfural

Abstract

Chiral cyclopentenones are important precursors in the asymmetric synthesis of target molecules. In particular, C-2 amino cyclopentenones could be utilised as intermediates towards antitumor natural products. On the basis of our previous experience, we report an environmentally friendly protocol for the synthesis of bifunctionalized cyclopentenones in water from furfural. The use of water and MW gives high regioselectivity and good to excellent yields. The reaction can be realized in short times with various nucleophiles.
Graphical abstract: Water excellent solvent for the synthesis of bifunctionalized cyclopentenones from furfural
Image result for M. Nardi, chimica
Università della Calabria
Department
  • Dipartimento di Chimica e Tecnologie Chimiche - CTC
  • Research experience

    • Oct 2014–present
      Visiting Lectur
      The School of Pharmacy · School of Pharmacy · Prof Steve Brocchini
      United Kingdom · London
    • Jan 2014–present
      PostDoc Position
      Università della Calabria · Department of Pharmacy, Health and Nutritional Sciences
      Italy · Rende
    • Mar 2001–Sep 2014
      PostDoc
      Università della Calabria · Department of Management
      Italy · Rende
    • Mar 2001–Dec 2013
      PostDoc Position
      Università della Calabria · Dipartimento di Chimica e Tecnologie Chimiche - CTC · Prof Giovanni Sindona
      Italy · Rende
Image result for Dipartimento di Chimica, Università della Calabria
Image result for Dipartimento di Chimica, Università della Calabria
Dipartimento di Chimica, Università della Calabria

1 Estevão, Mónica S.; Afonso, Carlos A.M.; Tetrahedron Letters; vol. 58; nb. 4; (2017); p. 302 - 304
2  Green Chemistry; vol. 19; nb. 1; (2017); p. 164 - 168



“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
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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