Monday 26 December 2016

Eco-Friendly, Catalyst and Solvent-Free, Synthesis of Acetanilides and N-Benzothiazole-2-yl-acetamides




N-(o-Tolyl)acetamide (3b) White solid, 51.5 mg, 71% yield; m.p. 108.4-109.0 °C (Lit.27 108-109 °C); IR (KBr) n / cm-1 3291, 1647, 1587, 1527, 1458, 1369, 1271, 1116, 1039, 933, 854, 756, 698, 651, 607; 1H NMR (500 MHz, CDCl3) d 2.19 (s, 3H, CH3), 2.30 (s, 3H, CH3), 7.10 (t, 1H, J 7.5 Hz, CH), 7.21 (t, 1H, J 8.0 Hz, CH), 7.71 (d, 1H, J 8.0 Hz, CH); 13C NMR (125 MHz, CDCl3) d 17.8, 24.2, 123.7, 125.4, 126.7, 129.7, 130.5, 135.6, 168.6.






Short ReportJ. Braz. Chem. Soc. 2016

Eco-Friendly, Catalyst and Solvent-Free, Synthesis of Acetanilides and N-Benzothiazole-2-yl-acetamides

Silvio Cunha; Lourenço L. B. de Santana
An expeditious and green synthesis of acetamides is described in good yield without external heating, and with simple purification. 

This paper is part of the PubliSBQ Special Issue in honor of the late Prof Angelo da Cunha Pinto.

http://dx.doi.org/10.21577/0103-5053.20160265

Published online: September 27, 2016.


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Synthesis of symmetrical pyridines by iron-catalyzed cyclization of ketoxime acetates and aldehydes





Synthesis of symmetrical pyridines by iron-catalyzed cyclization of ketoxime acetates and aldehydes


Green Chem., 2017, Advance Article
DOI: 10.1039/C6GC03137D, Paper
YuKun Yi, Mi-Na Zhao, Zhi-Hui Ren, Yao-Yu Wang, Zheng-Hui Guan
A facile iron-catalyzed cyclization of aldehydes with ketoxime acetates for the synthesis of multisubstituted symmetrical pyridines has been developed.


Synthesis of symmetrical pyridines by iron-catalyzed cyclization of ketoxime acetates and aldehydes

YuKun Yi,a   Mi-Na Zhao,a   Zhi-Hui Ren,a  Yao-Yu Wanga and   Zheng-Hui Guan*a  

*
Corresponding authors
a
Key Laboratory of Synthetic and Nature Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an 710127, P.R. China
 E-mail: guanzhh@nwu.edu.cn
Green Chem., 2017, Advance Article

DOI: 10.1039/C6GC03137D























http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C6GC03137D?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract


A novel and facile iron-catalyzed cyclization of ketoxime acetates and aldehydes for the green synthesis of substituted pyridines has been developed. In the presence of a FeCl3 catalyst, this reaction exhibited a good functional group tolerance to produce 2,4,6-triarylsubstituted symmetrical pyridines in high yields in the absence of any additive. A gram-scale reaction sequence was performed to demonstrate the scaled-up applicability of this synthetic method.




4-Phenyl-2,6-di-p-tolylpyridine (3bb). Yield 70% (47.0 mg); Yellow solid; mp 148-150 o C; S-3

1 H NMR (400 MHz, CDCl3): δ 8.09 (d, J = 8.0 Hz, 4H), 7.82 (s, 2H), 7.72 (d, J = 7.2 Hz, 2H), 7.52-7.45 (m, 3H), 7.31 (d, J = 8.0 Hz, 4H), 2.42 (s, 6H).

13C NMR (100 MHz, CDCl3): δ 157.3, 149.9, 139.2, 138.9, 136.8, 129.4, 129.0, 128.8, 127.1, 126.9, 116.5, 21.3.

HRMS Calcd (ESI) m/z for C25H22N: [M+H] + 336.1747. Found: 336.1731.





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Friday 2 December 2016

Product Control Using Substrate Design



Product Control Using Substrate Design

New class of cyclic Weinreb amides for oxidative C-H olefination or Heck reaction

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