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Showing posts with label 1. Show all posts
Showing posts with label 1. Show all posts

Sunday, 12 March 2017

1,3-Diphenylisoquinoline







1,3-Diphenylisoquinoline (3a). Pale-yellow solid (103.5 mg, 92%),

 mp 78-79 oC (lit.24,  73-74.5 oC). 24 J. D. Tovar and T. M. Swager, J. Org. Chem., 1999, 64, 6499

1H NMR (500 MHz, CDCl3) δ 8.25-8.23 (m, 2H), 8.15-8.14 (m, 1H), 8.09 (s, 1H), 7.95-7.93 (m, 1H), 7.84-7.83 (m, 2H), 7.70-7.67 (m, 1H), 7.59-7.50 (m, 6H), 7.44-7.40 (m, 1H);

13C NMR (125 MHz, CDCl3) δ 160.5, 150.3, 140.1, 139.8, 138.0, 130.4, 130.2, 128.8, 128.7, 128.6, 128.4, 127.7, 127.6, 127.2, 127.0, 126.0, 115.8.


Efficient synthesis of isoquinolines in water by a Pd-catalyzed tandem reaction of functionalized alkylnitriles with arylboronic acids
Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC00267J, Paper
Kun Hu, Linjun Qi, Shuling Yu, Tianxing Cheng, Xiaodong Wang, Zhaojun Li, Yuanzhi Xia, Jiuxi Chen, Huayue Wu
Pd-catalyzed tandem reaction of functionalized alkylnitriles with arylboronic acids for the synthesis of diverse isoquinolines in water.

Efficient synthesis of isoquinolines in water by a Pd-catalyzed tandem reaction of functionalized alkylnitriles with arylboronic acids

Kun Hu,a   Linjun Qi,a   Shuling Yu,a   Tianxing Cheng,a  Xiaodong Wang,a   Zhaojun Li,b   Yuanzhi Xia,a  Jiuxi Chen*a and   Huayue Wua  
 
*Corresponding authors
aCollege of Chemistry & Materials Engineering, Wenzhou University, Wenzhou 325035, China
E-mail: jiuxichen@wzu.edu.cn
bInstitute of Agricultural Resources and Regional Planning, Chinese Academy of Agricultural Sciences, Key Laboratory of Plant Nutrition and Fertilizer, Ministry of Agriculture, Beijing, China
Green Chem., 2017, Advance Article

DOI: 10.1039/C7GC00267J, 
A palladium-catalyzed tandem reaction of 2-(cyanomethyl)benzonitriles or 2-(2-carbonylphenyl)acetonitriles with arylboronic acids in water has been developed for the first time. This reaction features good functional group tolerance and provides a new strategy for the synthesis of diverse isoquinolines under mild conditions. The use of water as the reaction medium makes the synthesis process environmentally benign. Preliminary mechanistic experiments indicate that the major reaction pathway involves carbopalladation of the C(sp3)–cyano group and subsequent intramolecular cyclization findings that were further supported by density functional theory (DFT) calculations.

Capture

STR1

1,3-Diphenylisoquinoline (3a). Pale-yellow solid (103.5 mg, 92%),
 mp 78-79 oC (lit.24,  73-74.5 oC). 24 J. D. Tovar and T. M. Swager, J. Org. Chem., 1999, 64, 6499
1H NMR (500 MHz, CDCl3) δ 8.25-8.23 (m, 2H), 8.15-8.14 (m, 1H), 8.09 (s, 1H), 7.95-7.93 (m, 1H), 7.84-7.83 (m, 2H), 7.70-7.67 (m, 1H), 7.59-7.50 (m, 6H), 7.44-7.40 (m, 1H); 
13C NMR (125 MHz, CDCl3) δ 160.5, 150.3, 140.1, 139.8, 138.0, 130.4, 130.2, 128.8, 128.7, 128.6, 128.4, 127.7, 127.6, 127.2, 127.0, 126.0, 115.8. 
//////// isoquinoline, pd-catalyzed, arylboronic acids



Wednesday, 8 March 2017

1,2-bis((5-bromopyridine-2-yl)diazene oxide

 
Figure
1,2-bis((5-bromopyridine-2-yl)diazene oxide
1H NMR (DMSO): δ in ppm (integral, multiplicity, Hz) 8.83 (1H, dd, 0.56, 2.38) 8.82 (1H, dd, 0.64, 2.49) 8.48 (1H, dd, 2.40, 8.65) 8.28 (1H, dd, 0.60, 8.64) 8.02 (1H, dd, 0.67,8.69)
13C NMR (DMSO): δ in ppm (type of carbon) 150.33 (C-H), 149.48 (C-H), 142.74 (C-H), 140.86 (C-H), 119.60 (C-H), 119.46 (C-H)
LC/MS data (ESI) 358.8981 ([M+H]+ ), 380.8789 ([M+Na]+ )

Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.6b00433
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Friday, 28 October 2016

1,1-Dimethyl-3-(pyridin-2-yl)urea



Solvent- and halide-free synthesis of pyridine-2-yl substituted ureas through facile C-H functionalization of pyridine N-oxides

Green Chem., 2016, Advance Article
DOI: 10.1039/C6GC02556K, Paper
Valentin A. Rassadin, Dmitry P. Zimin, Gulnara Z. Raskil'dina, Alexander Yu. Ivanov, Vadim P. Boyarskiy, Semen S. Zlotskii, Vadim Yu. Kukushkin
A solvent- and halide-free atom-economical synthesis of practically useful pyridine-2-yl substituted ureas utilizes pyridine N-oxides and dialkylcyanamides.


Solvent- and halide-free synthesis of pyridine-2-yl substituted ureas through facile C–H functionalization of pyridine N-oxides


*
Corresponding authors
a
Institute of Chemistry, Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russia
E-mail: v.rassadin@spbu.ruv.kukushkin@spbu.ru
b
Ufa State Petroleum Technological University, Kosmonavtov 1, Ufa, Bashkortostan, Russia
c
Research Park SPbSU, Center for Magnetic Resonance, Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russia
Green Chem., 2016, Advance Article

DOI: 10.1039/C6GC02556K






























A novel solvent- and halide-free atom-economical synthesis of practically useful pyridine-2-yl substituted ureas utilizes easily accessible or commercially available pyridine N-oxides (PyO) and dialkylcyanamides. The observed C–H functionalization of PyO is suitable for the good-to-high yielding synthesis of a wide range of pyridine-2-yl substituted ureas featuring electron donating and electron withdrawing, sensitive, or even fugitive functional groups at any position of the pyridine ring (63–92%; 19 examples). In the cases of 3-substituted PyO, the C–H functionalization occurs regioselectively providing a route for facile generation of ureas bearing a 5-substituted pyridine-2-yl moiety.



1,1-Dimethyl-3-(pyridin-2-yl)urea







1,1-Dimethyl-3-(pyridin-2-yl)urea (4a)3 : From pyridine 1-oxide (1a) (95.0 mg, 1.00 mmol) and dimethylcyanamide (2a) (105 mg, 1.50 mmol), compound 4a (147 mg, 89%) was obtained according to GP1 as a yellow oil, which was then crystalized in the freezer to give pale yellow solid, m.p. = 42.6–43.5 °C, lit.4 m.p. = 44–47 °C (EtOAc/hexane), Rf = 0.25 (EtOAc). 1H NMR (400 MHz, CDCl3): δ = 3.00 (s, 6 H, NCH3), 6.88 (ddd, J = 7.3, 5.0, 0.9 Hz, 1 H), 7.30 (br. s, 1 H), 7.60 (ddd, J = 8.5, 7.3, 1.9 Hz, 1 H), 8.02 (dt, J = 8.5, 0.9 Hz, 1 H), 8.14 (ddd, J = 5.0, 1.9, 0.9 Hz, 1 H) ppm. 13C NMR (101 MHz, CDCl3): δ = 36.3 (2 С, CH3), 113.0 (CH), 118.1 (CH), 138.0 (CH), 147.3 (CH), 152.8 (C), 154.8 (C) ppm. NMR data are consistent with previously reported.3 HRMS (ESI), m/z: [M + H]+ calcd. for C8H12N3O+ : 166.0975; found: 166.0977.


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Thursday, 6 October 2016

A Rapid microwave assisted synthesis of novel 1,4-dihydropyridines derivatives under aqueous medium



Chemistry & Biology Interface

July-August 2012, Volume 2, No.4

July-August 2012, Volume 2, No.4
Chemistry & Biology Interface, 2012, 2, 4, 206-257
(ISSN: 2249 – 4820)


A Rapid microwave assisted synthesis of novel 1,4-dihydropyridines derivatives under aqueous medium
Shailesh Thakrar, Dhairya Bhavsar, Vicky Jain, Anamik Shah 

Chemistry & Biology Interface, 2012, 2, 4, 220-227 pg 220-227, Department of Chemistry, Saurashtra University, Rajkot-360005, India
 
[Full Text-PDF]

Keywords: 1, 4-dihydro pyridines, Pyrazole aldehyde, One-pot, Microwave, Aqueous medium,
Fe+3 montmorillonite clay K-10, HY-zeolite.
Abstract: An environment friendly synthesis of 1,4-dihydropyridine derivatives was developed by one pot multi component reaction of pyrazole aldehyde, EAA/MAA, 3-amino crotononitrile and Fe+3 montmorillonite clay K-10/ HY-zeolite under microwave irradiation in aqueous medium. The structures of all synthesized compounds were well characterized by Mass, FT-IR, 1H NMR and elemental analysis.

Methyl 5-cyano-1,4-dihydro-2,6-dimethyl- 4-(1,3-diphenyl-1H-pyrazol-4-yl)pyridine- 3-carboxylate (5a): MP: 182-184 oC; IR (cm-1): 3489, 3367, 3198, 2974, 2897, 2332, 2260, 1707, 1660, 1587, 1519, 1435, 1356, 1282, 744, 688. MS: m/z = 426.17; 1H NMR (DMSO-d6) δ ppm: 2.14(s, 6H), 2.58(s, 3H), 4.91(s, 1H), 6.91-6.99(d, 2H), 7.20-7.22(t, 2H), 7.29-7.31(t, 1H), 7.45-7.49(t, 2H), 7.60-7.62(d, 1H), 7.71-7.73(d, 2H), 7.95(s, 1H), 8.74(s, 1H). MS: m/z: 410.17; Anal. Calcd. for C25H22N4O2: C, 73.15; H, 5.40; N,13.65; O,7.80; Found: C, 73.06; H, 5.36; N, 13.61; O,7.79(%).





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Sunday, 18 September 2016

Synthesis and Antifungal Activity Against Candida Strains of Mesoionic System Derived From 1,3-Thyazolium-5-thiolate






General procedure for the preparation of ten newly synthetized compounds - 2-(p-chlorophenyl)-3-methyl-4- (p-isopropylphenyl)-1,3-thiazolium-5-(N-arylacetamide)thio chloridrates 7a-j Mesoionic 2-(p-chlorophenyl)-3-methyl-4-(pisopropylphenyl)-1,3-thiazolium-5-thiolate 5 (278 mmol) was dissolved in hot ethanol and then 2-chloro-Narylacetamides 6a-j (278 mmol) were added. The system was refluxed for 4 h and then concentrated at reduced pressure, giving a yellow-orange solid.


R1, R2 =H, H
7a


2-(p-Chlorophenyl)-3-methyl-4-(p-isopropylphenyl)-1,3- thiazolium-5-(N-phenylacetamide)thio chloridrate 7a Yield: 92.13%;

m.p.: 130-132 °C; anal. calcd.: C, 60.58; H, 4.69; N, 5.43; S, 12.44; found: C, 60.60; H, 4.70; N, 5.42; S, 12.42;

IR (KBr) νmax / cm-1 3181 (NH), 3003 (CHAr.), 2958 (CHAlif.), 1680 (C=O), 1599, 1551, 1491 (C=C and C=N of aromatic and heterocyclic rings), 1442 (C–N of N–CH3), 1404 (C–N), 1092 (C–Cl), 1001, 922 (CHAr.), 756 (NH), 557, 537 (C–C);

1 H NMR (200 MHz, CDCl3) delta
1.30 (d, 6H, J 6.9 Hz, H-16, H-16’),
2.98 (sept, 1H, H-15), 3.79 (s, 2H, H-17),
3.84 (s, 3H, H-10), 7.09 (t, 2H, J 7.3 Hz, H-23),
7.28-7.34 (m, 4H, H-13, H-13’, H-21, H-25),
7.60 (d, 2H, J 8.1 Hz, H-8, H-8’),
7.73 (d, 2H, J 7.9 Hz, H-12, H-12’),
7.86-7.93 (t, 4H, J 7.3 Hz, H-7, H-7’, H-22, H-24),
11.02 (s, 1H, H-19);


13C NMR (50 MHz, CDCl3)
delta 170.21 (C-2), 166.81 (C-18), 152.68 (C-14),
140.28 (C-4), 138.93 (C-9), 132.04 (C-20), 131.64 (C-7, C-7’), 130.89 (C-12, C-12’),
130.27 (C-8, C-8’), 128.69 (C-22, C-24), 127.54 (C-13, C-13’),
124.09 (C-23), 123.79 (C-11), 123.59 (C-6),
120.28 (C-21, C-25), 42.24 (C-17), 40.92 (C-10), 34.21 (C-15), 23.76 (C-16, 16’).








Peixoto IN, Souza HDS, Lira BF, Silva DF, Lima EO, Barbosa-Filho JM, et al. Synthesis and Antifungal Activity AgainstCandida Strains of Mesoionic System Derived From 1,3-Thyazolium-5-thiolate. J. Braz. Chem. Soc. 2016;27(10):1807-1813

*e-mail: athayde-filho@quimica.ufpb.br
J. Braz. Chem. Soc. 2016, 27(10), 1807-1813

Synthesis and Antifungal Activity Against Candida Strains of Mesoionic System Derived From 1,3-Thyazolium-5-thiolate


Isabelle N. Peixoto; Helivaldo D. S. Souza; Bruno F. Lira; Daniele F. Silva; Edeltrudes O. Lima; José M. Barbosa-Filho; Petrônio F. de Athayde-Filho

Ten new mesoionic derivatives from the 1,3-thiazolium-5-thiolate system with substituted acetamides were synthesized, had their potential as new drug evaluated in an in silico study and in their activity as antifungal against strains of Candida albicans.

http://dx.doi.org/10.5935/0103-5053.20160063

Published online: February 26, 2016
http://jbcs.sbq.org.br/imagebank/pdf/151131AR.pdf

Petrônio Filgueiras Athayde-Filho
Petrônio F. de Athayde-Filho
Universidade Federal da Paraíba

Universidade Federal da Paraíba
https://www.researchgate.net/profile/Petronio_Athayde-Filho

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Dubrovnik, croatia


Map of Dubrovnik
Dubrovnik
City in Croatia
Dubrovnik is a city in southern Croatia fronting the Adriatic Sea. It's known for its distinctive Old Town, encircled with massive stone walls completed in the 16th century. Its well-preserved buildings range from baroque St. Blaise Church to Renaissance Sponza Palace and Gothic Rector’s Palace, now a history museum. Paved with limestone, the pedestrianized Stradun (or Placa) is lined with shops and restaurants.


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Saturday, 9 July 2016

tert-butyl-(E)-3-(1,1,1-trifluoro-4-oxo-4-phenylbut-2-en-2-yl)-1H-indole-1-carbox ylate



tert-butyl-(E)-3-(1,1,1-trifluoro-4-oxo-4-phenylbut-2-en-2-yl)-1H-indole-1-carbox ylate

yellow solid (0.58 g, 70% yield), mp = 79 - 80 °C. 1H NMR (300 MHz, CDCl3) δ 8.07 (d, J = 8.4 Hz, 1H), 7.85 (s, 1H), 7.82 (d, J = 1.5 Hz, 1H), 7.66 (s, 1H), 7.52 (d, J = 7.5 Hz, 1H), 7.49 (t, J = 1.4 Hz, 1H), 7.38 (t, J = 7.7 Hz, 2H), 7.32 - 7.25 (m, 2H), 7.17 -7.12 (m, 1H), 1.65 (s, 9H). 13C NMR (75 MHz, CDCl3) δ 191.2, 149.1, 136.2, 134.9, 133.8, 132.4 (q, JC-F = 31.8 Hz), 131.1 (q, JC-F = 4.8 Hz), 128.7, 128.7, 128.6, 126.7, 124.9, 123.1, 122.8 (q, JC-F = 273.3 Hz), 119.9, 115.3, 111.1, 84.5, 28.1. 19F NMR (282 MHz, CDCl3) δ −66.9. HRMS (ESI) m/z calcd for C23H21F3NO3 [M+H]+ : 416.1468, found 416.1474.



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  • Supporting Info
  • MAHARASHTRA TRIBAL FOOD, MAHARASHTRA, MARATHI, INDIA






















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