An Efficient Synthesis of Nitrated Cycloalka[b]pyridines

Song Thi Le; Haruyasu Asahara; Nagatoshi Nishiwaki

doi:10.1055/s-0033-1341237

Synthesis, Inhaltsverzeichnis

Synthesis 2014; 46(16): 2175-2178
DOI: 10.1055/s-0033-1341237

paper

An Efficient Synthesis of Nitrated Cycloalka[b]pyridines

Song Thi Le

^aSchool of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan Fax: +81(887)572520 eMail: nishiwaki.nagatoshi@kochi-tech.ac.jp

,

Haruyasu Asahara

^aSchool of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan Fax: +81(887)572520 eMail: nishiwaki.nagatoshi@kochi-tech.ac.jp

^bResearch Center for Material Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan

,

Nagatoshi Nishiwaki*

^aSchool of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan Fax: +81(887)572520 eMail: nishiwaki.nagatoshi@kochi-tech.ac.jp

^bResearch Center for Material Science and Engineering, Kochi University of Technology, Tosayamada, Kami, Kochi 782-8502, Japan

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Abstract

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Abstract

The three-component ring transformation of 1-methyl-3,5-dinitro-2-pyridone with cycloalkanones of different ring sizes in the presence of ammonium acetate affords the corresponding nitrated cycloalka[b]pyridines in high yields. Furthermore, a double bond can be easily introduced into the product by changing the cycloalkanone into a cycloalkenone.

Key words

pyridines - multicomponent reaction - ketones - heterocycles - bicyclic compounds - ring transformation

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References

1a Nishiwaki N In Comprehensive Organic Synthesis . 2nd ed., Vol. 6 Elsevier; Oxford: 2014: 100-130
1b Balini R, Gabrietti S, Palmieri A, Petrini M. Curr. Org. Chem. 2011; 15: 1482
1c Ballini R, Barboni L, Fiorini D, Palmieri A, Petrini M. ARKIVOC 2006; (vi): 127
1d Adams JP, Peterson JR. J. Chem. Soc., Perkin Trans. 1 2000; 3695

2a Nishiwaki N, Ariga M In Topics in Heterocyclic Chemistry, Bioactive Heterocycles II . Vol. 8. Eguchi S. Springer; Berlin: 2007: 43-72
2b Tohda Y, Kawahara T, Eiraku M, Tani K, Nishiwaki N, Ariga M. Bull. Chem. Soc. Jpn. 1994; 67: 2176
2c Tohda Y, Eiraku M, Nakagawa T, Usami Y, Ariga M, Kawashima T, Tani K, Wanatabe H, Mori Y. Bull. Chem. Soc. Jpn. 1990; 63: 2820

3 Nishiwaki N, Hirao S, Sawayama J, Saigo K. Heterocycles 2012; 84: 115

4a Henry C, Haupt A, Turner SC. J. Org. Chem. 2009; 74: 1932
4b Sagitullina GP, Garkushenko AK, Vinokurova YO, Nyrkova VA, Atavin EG, Sagitullin RS. Russ. J. Org. Chem. 2009; 45: 1045

5 Tohda Y, Ariga M, Kawashima T, Matsumura E. Bull. Chem. Soc. Jpn. 1987; 60: 201

The TCRT of 3-methyl-5-nitro-4-pyrimidinone with ketone in the presence of NH₄OAc proceeds efficiently to afford pyrimidines, nitropyridones, and aminopyridines, see:

6a Nishiwaki N, Sugimoto R, Saigo K, Kobiro K. Tetrahedron Lett. 2013; 54: 956
6b Nishiwaki N, Yamashita K, Azuma M, Adachi T, Tamura M, Ariga M. Synthesis 2004; 1996
6c Nishiwaki N, Azuma M, Tamura M, Hori K, Tohda Y, Ariga M. Chem. Commun. 2002; 2170

7 Le TS, Asahara H, Kobiro K, Sugimoto R, Saigo K, Nishiwaki N. Asian J. Org. Chem. 2014; 3: 297
8 Yamada S, Goto T, Yamaguchi T, Aihara K, Kogi K, Narita S. Chem. Pharm. Bull. 1995; 43: 421
9 Yamada S, Goto T, Shimanuki E, Narita S. Chem. Pharm. Bull. 1994; 42: 718
10 Marcelis AT. M, van der Plas HC. Tetrahedron 1989; 45: 2693

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