New reactivity of nitropyrimidinone: Ring transformation and N-C transfer reactions

Synlett

Volumn , Issue 4, 2004, Pages 703-707

  Nishiwaki, Nagatoshi ^a   Matsushima, Kazuo ^a   Chatani, Miki ^a   Tamura, Mina ^a   Ariga, Masahiro ^a  

^a OSAKA KYOIKU UNIVERSITY   (Japan)

Author keywords

Diazepine; Functionalized enamine; Nitropyrimidinone; Pyrazole; Pyridone

Indexed keywords

1,4 DIAZEPINE; 3 METHYL 5 NITROPYRIMIDIN 4(3H) ONE; CARBENOID; DIAZEPINE DERIVATIVE; ENAMINE; HYDRAZINE DERIVATIVE; NITROPYRIMIDINONE; PYRAZOLE DERIVATIVE; PYRIMIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

ALKALINITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMER; NITROGEN CARBON TRANSFER REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING TRANSFORMATION REACTION; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

EID: 1642306143     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817788     Document Type: Article

References (16)

1. 2b in 43% overall yield.
2. (a) Nishiwaki, N.; Adachi, T.; Matsuo, K.; Wang, H.-P.; Matsunaga, T.; Tohda, Y.; Ariga, M. J. Chem. Soc., Perkin Trans. 1 2000, 27.
3. (b) Nishiwaki, N.; Matsunaga, T.; Tohda, Y.; Ariga, M. Heterocycles 1994, 38, 249.
4. Nishiwaki, N.; Tohda, Y.; Ariga, M. Synthesis 1997, 1277.
5. Nishiwaki, N.; Azuma, M.; Tamura, M.; Hori, K.; Tohda, Y.; Ariga, M. Chem. Commun. 2002, 2170.
6. Nishiwaki, N.; Mizukawa, Y.; Terai, R.; Tohda, Y.; Ariga, M. Arkivoc 2000, 1, 103.
7. Kiyama, R.; Fuji, M.; Hara, M.; Fujimoto, M.; Kawabata, T.; Nakamura, M. ; Fujishita, T. Chem. Pharm. Bull. 1995, 43, 450.
8. (a) Milata, V. Aldrichimica Acta 2001, 34, 20.
9. (b) Takamura, S.; Yoshimiya, T.; Kameyama, S.; Nishida, A.; Yamamoto, H. ; Noguchi, M. Synthesis 2000, 637.
10. (b) Juki, L.; Svete, J.; Stanovnik, B. J. Heterocycl. Chem. 2001, 38, 869.
11. Menozzi, G.; Mosti, L.; Schenone, P. J. Heterocycl. Chem. 1987, 24, 1669.
12. Pyrazoles having an ethoxycarbonyl group are widely used for synthetic intermediates of agrochemicals such as insecticides, fungicides, herbicides and so on, see: (a) Kitajima, T.; Tomiya, K.; Kodaka, K. Jpn. Kokai Tokkyo Koho, JP 2000212166, 2000; Chem. Abstr., 2000, 133, 120326. (b) Okimura, N.; Tanaka, T.; Fukuchi, T.; Okada, I. Jpn. Kokai Tokkyo Koho, JP 04021671, 1992; Chem. Abstr., 1992, 117, 2830. (c) Ishii, T.; Kuwazuka, T.; Shimotori, H.; Tanaka, Y.; Ishikawa, K. Jpn. Kokai Tokkyo Koho, JP 01106866, 1989; Chem. Abstr., 1989, 111, 194759. (d) The NOESY spectrum of 7o showed correlation between the phenyl group and the methyl one that was derived from the acetyl group of 3a.
13. Pyrazoles having an ethoxycarbonyl group are widely used for synthetic intermediates of agrochemicals such as insecticides, fungicides, herbicides and so on, see: (a) Kitajima, T.; Tomiya, K.; Kodaka, K. Jpn. Kokai Tokkyo Koho, JP 2000212166, 2000; Chem. Abstr., 2000, 133, 120326. (b) Okimura, N.; Tanaka, T.; Fukuchi, T.; Okada, I. Jpn. Kokai Tokkyo Koho, JP 04021671, 1992; Chem. Abstr., 1992, 117, 2830. (c) Ishii, T.; Kuwazuka, T.; Shimotori, H.; Tanaka, Y.; Ishikawa, K. Jpn. Kokai Tokkyo Koho, JP 01106866, 1989; Chem. Abstr., 1989, 111, 194759. (d) The NOESY spectrum of 7o showed correlation between the phenyl group and the methyl one that was derived from the acetyl group of 3a.
14. Pyrazoles having an ethoxycarbonyl group are widely used for synthetic intermediates of agrochemicals such as insecticides, fungicides, herbicides and so on, see: (a) Kitajima, T.; Tomiya, K.; Kodaka, K. Jpn. Kokai Tokkyo Koho, JP 2000212166, 2000; Chem. Abstr., 2000, 133, 120326. (b) Okimura, N.; Tanaka, T.; Fukuchi, T.; Okada, I. Jpn. Kokai Tokkyo Koho, JP 04021671, 1992; Chem. Abstr., 1992, 117, 2830. (c) Ishii, T.; Kuwazuka, T.; Shimotori, H.; Tanaka, Y.; Ishikawa, K. Jpn. Kokai Tokkyo Koho, JP 01106866, 1989; Chem. Abstr., 1989, 111, 194759. (d) The NOESY spectrum of 7o showed correlation between the phenyl group and the methyl one that was derived from the acetyl group of 3a.
15. Pyrazoles having an ethoxycarbonyl group are widely used for synthetic intermediates of agrochemicals such as insecticides, fungicides, herbicides and so on, see: (a) Kitajima, T.; Tomiya, K.; Kodaka, K. Jpn. Kokai Tokkyo Koho, JP 2000212166, 2000; Chem. Abstr., 2000, 133, 120326. (b) Okimura, N.; Tanaka, T.; Fukuchi, T.; Okada, I. Jpn. Kokai Tokkyo Koho, JP 04021671, 1992; Chem. Abstr., 1992, 117, 2830. (c) Ishii, T.; Kuwazuka, T.; Shimotori, H.; Tanaka, Y.; Ishikawa, K. Jpn. Kokai Tokkyo Koho, JP 01106866, 1989; Chem. Abstr., 1989, 111, 194759. (d) The NOESY spectrum of 7o showed correlation between the phenyl group and the methyl one that was derived from the acetyl group of 3a.
16. Kopp, M.; Lancelot, J.-C.; Dallemagne, P.; Rault, S. J. Heterocycl. Chem. 2001, 38, 1045.