DR ANTHONY MELVIN CRASTO,WorldDrugTracker, helping millions, A 90 % paralysed man in action for you, I am suffering from transverse mylitis and bound to a wheel chair, With death on the horizon, nothing will not stop me except God................DR ANTHONY MELVIN CRASTO Ph.D ( ICT, Mumbai) , INDIA 25Yrs Exp. in the feld of Organic Chemistry,Working for GLENMARK GENERICS at Navi Mumbai, INDIA. Serving chemists around the world. Helping them with websites on Chemistry.Million hits on google, world acclamation from industry, academia, drug authorities for websites, blogs and educational contribution

Thursday, 9 November 2017

2-Phenylfuran

STR3
2-Phenylfuran
17113-33-6 cas
STR1 STR2
2-Phenylfuran (3v) [15]: According to the general procedure I and purification by column chromatography (100% PE) yielded 3v (35.9 mg, 50%) and the general procedure II yielded 3s (35.1 mg, 49%) as a white solid . 1 H NMR (400 MHz, CDCl3) δ 7.68-7.66 (m 2H), 7.46 (s, 1H), 7.40-7.35 (m, 2H), 7.26-7.23 (m, 1H), 6.645-6.639 (m, 1H), 6.461-6.457 (m, 1H). LRMS (ESI) calcd for [M+H]+ C10H9O 145.1, found 145.1.
15 Zhou, C.-Y.; Chan, P. W. H.; Che, C.-M. Org. Lett. 2006, 8, 325.

Visible-Light Photoredox in Homolytic Aromatic Substitution: Direct Arylation of Arenes with Aryl Halides

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering, and Materials Science, Soochow University, 199 RenAi Road, Suzhou, Jiangsu 215123, China
Org. Lett.201315 (11), pp 2664–2667
DOI: 10.1021/ol400946k
 

Abstract

Abstract Image
Direct arylation of unactivated arenes or heteroarenes with aryl halides could be carried out in the presence of potassium tert-butoxide and dimethyl sulfoxide under visible-light irradiation. Ir(ppy)3was found to be an effective photoredox catalyst for this reaction. The reactions of aryl iodides occurred at room temperature. Elevated temperature was required for aryl bromides. Homolytic aromatic substitution was proposed to be the operative reaction pathway.
Predicts
1H NMR
STR1
13C NMR
STR2
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more info
Open Babel bond-line chemical structure with annotated hydrogens.<br>Click to toggle size.
<sup>1</sup>H NMR spectrum of C<sub>10</sub>H<sub>8</sub>O<sub></sub> in CDCL3 at 400 MHz.<br>Click to toggle size.

Shifts

IndexNameShift (ppm)
19H76.582
1H17.655
5H57.655
15H66.885
11H27.415
7H47.415
9H37.362
17H87.471

“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

 

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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
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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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Learn spectroscopy,1-chloro-2,2- dimethyl propane.PROBLEM 2

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1-chloro-2,2- dimethyl propane.
(C5H11Cl)





13C NMR


This 13C spectrum exhibits resonances at the following chemical shifts:
Shift (ppm)
57.3
33.1
27.3





NMR IS EASY

EVEN MOM CAN TEACH YOU


Image result for 1-chloro-2,2- dimethyl propane NMR

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“ORGANIC SPECTROSCOPY 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

Saturday, 4 November 2017

3.4. 1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid

Laura Beswick

Laura Beswick

2nd degree connection

PhD Student at Keele University


Keele University




Gavin J. Miller

Gavin J. Miller

2nd degree connection

Lecturer in Organic Chemistry at Keele University




3.4. 1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid (4)

To a vigorously stirred solution of 1,2,3,4-tetra-O-acetyl-β-d-mannopyranose (3) (1.5 g, 4.30 mmol, 1.0 equiv.) in dichloromethane (20 mL) and water (10 mL) was added (2,2,6,6-tetramethylpiperidin-1-yl)oxyl radical (TEMPO) (336 mg, 2.2 mmol, 0.50 equiv.) and [bis(acetoxy)iodo]benzene (BAIB) (6.9 g, 21.5 mmol, 5.00 equiv.). The solution was stirred at RT for 5 h, whereupon TLC analysis (hexane/ethyl acetate, 1/1) showed complete conversion of starting material to a baseline Rf value spot. The reaction was quenched with aqueous Na2S2O3 solution (10% w/v, 30 mL), the organic layer removed and the aqueous layer acidified to pH 3 using 1M HCl, followed by extraction with ethyl acetate (2 × 30 mL). The organic extracts were combined, dried (MgSO4), filtered and concentrated in vacuo to afford 1,2,3,4-tetra-O-acetyl-β-d-mannuronic acid (4) as a white solid (1.2 g, 3.3 mmol, 75%). Rf = 0.81 (dichloromethane/methanol, 9/1);

 1H-NMR (300 MHz, CDCl3) δH5.96 (1H, d, J = 1.5 Hz, H1), 5.50 (1H, dd, J = 3.2, 1.5 Hz, H2), 5.48 (1H, appt, J = 9.1 Hz, H4), 5.21 (1H, dd, J = 9.1, 3.2 Hz, H3), 4.2 (1H, d, J = 9.1 Hz, H5), 2.21 (3H, s, C(O)CH3), 2.13 (3H, s, C(O)CH3), 2.10 (3H, s, C(O)CH3), 2.04 (3H, s, C(O)CH3).
 13C-NMR (100 MHz, CDCl3) δC 169.9 (C=O), 169.7 (C=O), 169.5 (C=O), 169.4 (C=O), 168.2 (C=O), 89.4 (C1), 72.3 (C5), 69.3 (C3), 66.9 (C2), 65.9 (C4), 20.4 (C(O)CH3), 20.4 (C(O)CH3), 20.3 (C(O)CH3), 20.2 (C(O)CH3); 
FT-HRMS NSI (ES) m/z Found: (M−H) 361.0767, C14H17O11 requires 361.0776; FT-IR vmax/cm−1 2986 (O–H), 1751 (C=O).







Molbank 2017 m947 sch001

Molbank 20172017(3), M947; doi:10.3390/M947
Communication
1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid
Laura Beswick and Gavin J. Miller *Orcid
Lennard-Jones Laboratory, School of Chemical and Physical Sciences, Keele University, Keele, Staffordshire ST5 5BG, UK
*
Correspondence: Tel.: +44-1782-734442
Received: 3 July 2017 / Accepted: 11 July 2017 / Published: 14 July 2017


Abstract

: 
1,2,3,4-Tetra-O-acetyl-β-d-mannuronic acid was synthesized in three steps from commercial d-mannose in 21% yield. Regioselective 6-O-tritylation followed by per-acetylation and 6-OTr removal using HBr/AcOH gave the required primary alcohol substrate, which was then oxidised to the target compound using TEMPO/BAIB. None of the synthetic steps required column chromatography and the product was fully characterized by 1H-NMR, 13C-NMR, 2D NMR, MS and IR.


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Image result for Keele University, Keele, Staffordshire

Keele University, Keele, Staffordshire


Image result for Lennard-Jones Laboratory, School of Chemical and Physical Sciences, Keele University,

Image result for Lennard-Jones Laboratory, School of Chemical and Physical Sciences, Keele University,



Image result for Lennard-Jones Laboratory, School of Chemical and Physical Sciences, Keele University,


Lennard-Jones Laboratory, School of Chemical and Physical Sciences, Keele University,

“ORGANIC SPECTROSCOPY 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

Learn spectroscopy, Valeric acid or pentanoic acid. PROBLEM 1

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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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