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Saturday, 2 June 2018

Catalyst-free three-component synthesis of highly functionalized 2,3-dihydropyrroles

Graphical abstract: Catalyst-free three-component synthesis of highly functionalized 2,3-dihydropyrroles

Catalyst-free three-component synthesis of highly functionalized 2,3-dihydropyrroles

 Author affiliations

Abstract

An efficient synthesis of fully substituted 2,3-dihydropyrroles has been achieved in one step through the three-component reaction of amines, aromatic aldehydes and α-ketoamides. This atom-economical and catalyst-free reaction is highly stereoselective and generates underexplored heterocycles in a single step. These compounds were examined in an enzymatic assay that led to the identification of potent α-glucosidase inhibitors, thereby demonstrating the utility of this novel methodology in medicinal chemistry.




N-(4-Chlorophenyl)-2-oxopropanamide (3a) Cl H N O O 3a Using 4-chloroaniline (1.0 g, 7.8 mmol), in accordance with General Procedure A, the title compound 3a was obtained (810 mg, 52% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.73 (s, 1H), 7.60 (d, J = 8.0 Hz, 2H), 7.34 (d, J = 8.0 Hz, 2H), 2.57 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 197.1, 157.6, 135.0, 130.6, 129.5, 121.1, 24.2. HRMS (ESI-TOF) m/z calcd. for C9H7NO2Cl- [M-H]- : 196.0171, found 196.0170






Friday, 27 April 2018

Tert-butyl (N-[3-[(3S,4R)-3-amino-4-fluoro-4-(hydroxymethyl)tetrahydrofuran-3-yl]-4-fluorophenyl]acetamide)

STR1

tert-butyl (N-[3-[(3S,4R)-3-amino-4-fluoro-4-(hydroxymethyl)tetrahydrofuran-3-yl]-4-fluorophenyl]acetamide)

STR1
1H-NMR (500 MHz, DMSO-d6): 1.31 (s, 9H), 2.02 (s, 3H), 3.21 (m, 1H), 3.88 (m, 1H), 3.94 (m, 1H), 4.03 (m, 1H), 4.13 (m, 1H), 4.74 (m, 1H), 5.07 (m, 1H), 7.08 (m, 1H), 7.43 (bs, 1H), 7.63 (m, 1H), 7.67 (m, 1H), 10.03 (s, 1H) .
STR2
13C-NMR (125 MHz, DMSO-d6): 24.3, 28.5, 60.8, 65.1, 72.6, 78.1, 78.9, 105.8, 116.4, 119.7, 120.8, 127.2, 136.2, 155.2, 156.4, 168.7.
str3
19F-NMR (470.6 MHz, DMSO-d6): -164.77, -117.26.

str4 str5
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.8b00069

Tuesday, 17 April 2018

Cookson’s Dione

Cyclopentadienebenzoquinone.png
Chemical Names:Cyclopentadienebenzoquinone; 1200-89-1; 1,4,4a,8a-Tetrahydro-1,4-methanonaphthalene-5,8-dione; 1,4-Methanonaphthalene-5,8-dione, 1,4,4a,8a-tetrahydro-; NSC 25329; 1,4,4a,8a-Tetrahydro-endo-1,4-methanonaphthalene-5,8-dione
Molecular Formula:C11H10O2
Molecular Weight:174.199 g/mol
str3
1H NMR (CDCl3, 400 MHz) δ = 1.41 (dt, J = 8.8, 1.5 Hz, 1H), 1.52 (dt, J = 8.8, 1.8 Hz, 1H), 3.20 (dd, J = 2.5, 1.5 Hz, 2H), 3.52 (m, 2H), 6.04 (t, J = 1.9 Hz, 2H), 6.54 (s, 2H).
13C NMR (CDCl3, 100 MHz) δ = 48.4 (2 × CH), 48.8 (CH), 48.9 (2 × CH), 135.4 (2 × CH), 142.1 (2 × CH), 199.5 (2 × CO)
O=C3C=CC(=O)C2C3C1C=CC2C1
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.8b00037
Abstract ImageWe report the use of a simple rotary evaporator as a semi-continuous UV photochemical reactor. By generation of a thin film from the rotation of a flask, better light penetration is achieved, and in this work we used high-power Hg lamps to enable the direct irradiation of molecules with UV light. The intramolecular [2 + 2] photocycloaddition of Cookson’s dione and the intermolecular [2 + 2] photocycloaddition of maleimide with 1-hexyne were used as test reactions to examine the effectiveness of this reactor. High productivities, equivalent to 210 g h–1, were obtained for the simple intramolecular reaction, demonstrating the scalability of the reactor. The effects of flask size, reaction mixture volume, and use of borosilicate or quartz glassware were also investigated.
 
 

Cookson’s Dione

COOKSON'S DIONE
CAS No.: 2958-72-7
1H NMR (CDCl3, 300 MHz) δ = 1.86 (d, J = 11.3, 1H), 2.02 (d, J = 11.3, 1H), 2.68 (m, 2H), 2.79 (m, 2H), 2.90 (m, 2H), 3.15 (m, 2H).
 
Figure
 
References 1. Clark, C. A.; Lee, D. S.; Pickering, S. J.; Poliakoff, M.; George, M. W. Org. Process Res. Dev. 2016, 20, 1792-1798. 2. Elliott, L. D.; Knowles, J. P.; Koovits, P. J.; Maskill, K. G.; Ralph, M. J.; Lejeune, G.; Edwards, L. J.; Robinson, R. I.; Clemens, I. R.; Cox, B.; Pascoe, D. D.; Koch, G.; Eberle, M.; Berry, M. B.; Booker-Milburn, K. I. Chem. Eur. J. 2014, 20, 15226-15232. 3. Marchand, A. P.; Allen, R. W. J. Org. Chem. 1974, 39, 1596-1596. 4. Elliott, L. D.; Berry, M.; Harji, B.; Klauber, D.; Leonard, J.; Booker-Milburn, K. I. Org. Process Res. Dev. 2016, 20, 1806-1811. 5. Hook, B. D. A.; Dohle, W.; Hirst, P. R.; Pickworth, M.; Berry, M. B.; Booker-Milburn, K. I. J Org Chem 2005, 70, 7558-7564.

ORGANIC SPECTROSCOPY INTERNATIONAL: Cookson's Dione

https://orgspectroscopyint.blogspot.com/search/label/Cookson’s%20Dione
 
Oct 3, 2016 - Cookson's Dione 125 W Batch Reaction A solution of Diels Alder adduct 3[3] (2.61 g, 15 mmol) in degassed EtOAc (150 ml) was irradiated with a pre-warmed 125 W medium pressure mercury lamp in a 150 ml batch reactor equipped with a. Pyrex immersion well for 15 min. The solvent was removed in ..
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Saturday, 31 March 2018

4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane

Image result for 4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane

4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane


http://orgsyn.org/demo.aspx?prep=v94p0234




 4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane (1) has the following physical and spectroscopic properties: Rf = 0.47 (3:97, ethyl acetate:pentane), the checkers report the following values for 1: Rf = 0.09 (3:97 ethyl acetate:pentane); R= 0.52 (10% EtOAc in hexanes); Merck silica gel 60 F254 plate; mp 38-39 °C; 

1H NMR pdf(CDCl3, 400 MHz) δ: 1.18 (t, = 8.4 Hz, 2H), 1.26 (s, 12H), 2.79 (t, J = 8.0 Hz, 2H), 7.16-7.22 (m, 1H), 7.23-7.32 (m, 4H); 

13C NMR pdf(CDCl3, 151 MHz) d: 25.0, 30.1, 83.2, 125.6, 128.1, 128.3, 144.6 [N.B. the carbon attached to boron was not observed due to quadrupolar relaxation]; 

HRMS (ESI+) calculated for C14H22BO2+ = 233.1707, mass found = 233.1710; 

IR (film): 3026, 2978, 2929, 1372, 1318, 1139, 848, 755, 703 cm-1

Anal. calcd for C14H21BO2: C, 72.44; H, 9.12. Found: C, 72.18; H, 9.28. 








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Tuesday, 27 March 2018

BRUSH UP YOUR NMR, 4-(3,5-Dichloropyridin-4-yl)morpholine

str1
3,5-Dichloro-4-morpholinopyridine
 
 5 as a light-orange solid.
 
1H NMR (CDCl3, 400 MHz): δ = 8.35 (2H, s), 3.84 (4H, m), 3.37 (4H, m);
 
13C NMR (CDCl3, 101 MHz): δ = 150.8, 149.3, 128.4, 67.4, 50.4;
 
HRMS–ESI+m/z [M + H]+ calcd for C9H11Cl2N2O+: 233.02429; found: 233.02446.
 
 
 
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.8b00009
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Clc2cncc(Cl)c2N1CCOCC1

Saturday, 24 March 2018

METHYL 2-(ACETYLTHIO)ACETATE

ChemSpider 2D Image | Methyl 2-(methylthio)acetate | C4H8O2S

Methyl 2-(methylthio)acetate

  • Molecular FormulaC4H8O2S
  • Average mass120.170 Da
  • 16630-66-3
  • S-Methylthioglycolate

DOI: 10.1021/acs.oprd.7b00378
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Monday, 19 March 2018

S-Acetylation of Thiols Mediated by Triflic Acid: A Novel Route to Thioesters

Abstract Image
This paper demonstrates an efficient, mild, and chemoselective synthesis of various thioesters via a HOTf-catalyzed S-acetylation of aromatic and aliphatic thiols using isopropenyl acetate as a cheap and convenient acetylating agent. During our tests, we also investigated the differences between the activities of metal triflates and triflic acid as catalysts in the acetylation of thiols. Finally, the potential of our concept has been increased by the implementation of Nafion as a heterogeneous catalyst for S-acetylation of thiols.

S-Acetylation of Thiols Mediated by Triflic Acid: A Novel Route to Thioesters

Faculty of ChemistryAdam Mickiewicz University in Poznańul. Umultowska 89b, 61-614 Poznań, Poland
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.7b00378
Publication Date (Web): March 12, 2018
Copyright © 2018 American Chemical Society
 
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Friday, 9 March 2018

NEW DRUG APPROVALS HITS 20 LAKH VIEWS IN 218 COUNTRIES

NEW DRUG APPROVALS

https://newdrugapprovals.org/
ALL ABOUT DRUGS, LIVE, BY DR ANTHONY MELVIN CRASTO, WORLDDRUGTRACKER, HELPING MILLIONS, 9 MILLION HITS ON GOOGLE, PUSHING BOUNDARIES,2.5 LAKH PLUS CONNECTIONS WORLDWIDE, 18 LAKH PLUS VIEWS ON THIS BLOG IN 216 COUNTRIES, THE VIEWS EXPRESSED ARE MY PERSONAL AND IN NO-WAY SUGGEST THE VIEWS OF THE PROFESSIONAL BODY OR THE COMPANY THAT I REPRESENT, USE CTRL AND+ KEY TO ENLARGE BLOG VIEW……………………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, I HAVE LOT TO ACHEIVE

Concise synthesis of ketoallyl sulfones through an iron-catalyzed sequential four-component assembly

 
Green Chem., 2018, 20,973-977
DOI: 10.1039/C7GC03719H, Communication
Fuhong Xiao, Chao Liu, Dahan Wang, Huawen Huang, Guo-Jun Deng
A three starting material four component reaction (3SM-4CR) strategy is described to prepare [small beta]-acyl allylic sulfones from methyl ketones, sodium sulfinates and dimethylacetamide (DMA) in an iron-catalyzed oxidative system.

Concise synthesis of ketoallyl sulfones through an iron-catalyzed sequential four-component assembly

 
Author affiliations

Abstract

A three starting material four component reaction (3SM-4CR) strategy is described to prepare β-acyl allylic sulfones from methyl ketones, sodium sulfinates and dimethylacetamide (DMA) in an iron-catalyzed oxidative system. In this process, DMA was used as a dual synthon to provide two carbons. A broad range of functional groups were tolerated in this reaction system.
 1-phenyl-2-(tosylmethyl)prop-2-en-1-one (3ab)
 
43.2 mg, 72% yield).
 
1 H NMR (400 MHz, CDCl3) δ 7.78 (d, J = 8.2 Hz, 2H), 7.68-7.65 (m, 2H), 7.55 (t, J = 7.4 Hz, 1H), 7.43 (t, J = 7.8 Hz, 2H), 7.30 (d, J = 8.3 Hz, 2H), 6.25 (s, 1H), 6.02 (s, 1H), 4.35 (s, 2H), 2.39 (s, 3H).
 
13C NMR (100 MHz, CDCl3) δ 194.7, 144.9, 136.1, 135.8, 135.7, 133.9, 132.6, 129.8, 129.6, 128.3, 128.2, 57.7, 21.6.
 
HRMS calcd. for: C17H17O3S+ [M+H]+ 301.08929, found 301.08908
 
STR1 STR2

1H NMR PREDICT




13C NMR PREDICT ABOVE

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Cc1ccc(cc1)S(=O)(=O)CC(=C)C(=O)c2ccccc2

Thursday, 15 February 2018

p-Aminophenol

STR1 STR2
p-Aminophenol [123-30-8].
M.p. 182 °C; 1H NMR (300 MHz, d6-DMSO): 4.37 (br s, 2H, NH2), 6.37-6.44 (m, 2HAr), 6.44-6.50 (m, 2HAr), 8.33 (br s, 1H, OH);
13C NMR (75 MHz, d6-DMSO): δ 115.2 (2 CHAr), 115.5 (2 CHAr), 140.7 (Cq Ar), 148.2 (Cq Ar);
IR (ATR) max: 3338, 3279, 1471; MS (ESI+ ): 110.1 ([M+H]+ , 100).
1D 1H, 7.4 spectrum for 4-Aminophenol

1D 1H ABOVE


2D [1H,1H]-TOCSY, 7.4 spectrum for 4-Aminophenol

2D [1H,1H]-TOCSY ABOVE

1D 13C, 7.4 spectrum for 4-Aminophenol

1D 13C ABOVE


1D DEPT90, 7.4 spectrum for 4-Aminophenol

1D DEPT90 ABOVE

1D DEPT135, 7.4 spectrum for 4-Aminophenol

1D DEPT135 ABOVE

2D [1H,13C]-HSQC, 7.4 spectrum for 4-Aminophenol

2D [1H,13C]-HSQC ABOVE

2D [1H,13C]-HMBC, 7.4 spectrum for 4-Aminophenol

2D [1H,13C]-HMBC ABOVE