A Facile One-Pot Synthesis of
Substituted Pyridine-2,4(1H,3H)-diones from Acyl(carbamoyl)ketene S,S-Acetals

Yunhui Li; Wenliang Li; Rui Zhang; Yang Zhou; Dewen Dong

doi:10.1055/s-0028-1083168

RSS-Feed abonnieren

Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.

https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml

Teilen / Bookmarken

Facebook Linkedin Weibo

PDF herunterladen

Synthesis 2008(21): 3411-3414
DOI: 10.1055/s-0028-1083168

PAPER

A Facile One-Pot Synthesis of Substituted Pyridine-2,4(1H,3H)-diones from Acyl(carbamoyl)ketene S,S-Acetals

Yunhui Li^a, Wenliang Li^a,b, Rui Zhang^b, Yang Zhou^b, Dewen Dong*^b
^a School of Chemistry and Environmental Engineering, Changchun University of Science and Technology, Changchun 130022, P. R. of China
^b Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, P. R. of China
Fax: +86(431)85098635; e-Mail: dwdong@ciac.jl.cn;

Weitere Informationen

Publikationsverlauf

Received 26 June 2008
Publikationsdatum:
16. Oktober 2008 (online)

Abstract
Volltext
Referenzen

Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

A facile and efficient one-pot synthesis of substituted pyridine-2,4(1H,3H)-diones has been developed. Subjected to N,N-dimethylformamide dimethyl acetal (DMFDMA) in N,N-dimethylformamide at 120 ˚C, a series of acyl(carbamoyl)ketene S,S-acetals were converted into the corresponding substituted pyridine-2,4(1H,3H)-diones in high yields.

Key words

annulation - N,N-dimethylformamide dimethyl acetal - Michael addition - α-oxoketene S,S-acetals - pyridine-2,4(1H,3H)-diones

References

For reviews on the synthesis and application of α-oxoketene S,S-acetals, see:
1a Dieter RK. Tetrahedron 1986, 42: 3029

Suche in Google Scholar
1b Tominaga Y. J. Heterocycl. Chem. 1989, 26: 11674

Suche in Google Scholar
1c Junjappa H. Ila H. Asokan CV. Tetrahedron 1990, 46: 5423

Suche in Google Scholar
1d Kolb M. Synthesis 1990, 171
1e Junjappa H. Ila H. Phosphorous, Sulfur Silicon Relat. Elem. 1994, 35
1f Junjappa H. Ila H. Mohanta PK. In Progress in Heterocyclic Chemistry Vol. 13: Gribble GH. Gilchrist LT. Pergamon Press; Oxford: 2001. Chap. 1. p.1-24

Suche in Google Scholar
2a Singh G. Purkayastha ML. Ila H. Junjappa H. J. Chem. Soc., Perkin Trans. 1 1985, 1289
2b Asokan CV. Ila H. Junjappa H. Synthesis 1987, 284
2c Patra PK. Suresh JR. Ila H. Junjappa H. Tetrahedron 1998, 54: 10167

Suche in Google Scholar
3a Apparao S. Datta A. Ila H. Synthesis 1985, 169
3b Datta A. Ila H. Junjappa H. Tetrahedron Lett. 1988, 29: 497

Suche in Google Scholar
3c Datta A. Ila H. Junjappa H. J. Org. Chem. 1990, 55: 5589

Suche in Google Scholar
4a Balu MP. Ila H. Junjappa H. Tetrahedron Lett. 1987, 28: 3023

Suche in Google Scholar
4b Dieter RK. Fishpaugh JR. J. Org. Chem. 1988, 53: 2031

Suche in Google Scholar
5a Dieter RK. Silks LA. Fishpaugh JR. Kastner ME. J. Am. Chem. Soc. 1985, 107: 4679

Suche in Google Scholar
5b Dieter RK. Fishpaugh JR. Silks LA. Tetrahedron Lett. 1982, 23: 3751

Suche in Google Scholar
6a Mahata PK. Venkatesh C. Kumar UKS. Ila H. Junjappa H. J. Org. Chem. 2003, 68: 3966

Suche in Google Scholar
6b Rudorf W.-D. Tetrahedron 1978, 34: 725

Suche in Google Scholar
6c Chauhan SMS. Junjappa H. Tetrahedron 1976, 32: 1779

Suche in Google Scholar
6d Chauhan SMS. Junjappa H. Tetrahedron 1976, 32: 1911

Suche in Google Scholar
6e Apparao S. Rahman A. Ila H. Synthesis 1982, 792
6f Singh LW. Gupta AK. Ila H. Junjappa H. Synthesis 1984, 516
6g Barun O. Ila H. Junjappa H. J. Org. Chem. 2000, 65: 1583

Suche in Google Scholar
7 Bi X. Dong D. Liu Q. Pan W. Zhao L. Li B. J. Am. Chem. Soc. 2005, 127: 4578

Crossref PubMed Suche in Google Scholar
8a Dong D. Bi X. Liu Q. Cong F. Chem. Commun. 2005, 35802
8b Bi X. Dong D. Li Y. Liu Q. Zhang Q. J. Org. Chem. 2005, 70: 10886

Suche in Google Scholar
9a Myrboh B. Asokan CV. Ila H. Junjappa H. Synthesis 1984, 50
9b Asokan CV. Ila H. Junjappa H. Synthesis 1985, 163
9c Asokan CV. Balu MP. Ila H. Junjappa H. Synthesis 1988, 727
9d Choi EB. Youn IK. Pak CS. Synthesis 1991, 15
10 Ouyang Y. Dong D. Pan W. Zhang J. Liu Q. Tetrahedron 2006, 62: 10111

Crossref Suche in Google Scholar
11 Pan W. Dong D. Ouyang Y. Wu R. Yang Y. Liu Q. Synthesis 2007, 2115

Thieme Connect
12 Ouyang Y. Dong D. Yu H. Liang Y. Liu Q. Adv. Synth. Catal. 2006, 348: 206

Crossref Suche in Google Scholar
13a Bernasconi CF. Schuck DF. Ketner RJ. Eventova I. Rappoport Z. J. Am. Chem. Soc. 1995, 117: 2719

Suche in Google Scholar
13b Bernasconi CF. Tetrahedron 1989, 45: 4017

Suche in Google Scholar
13c Bernasconi CF. Ketner RJ. Chen X. Rappoport Z. J. Am. Chem. Soc. 1998, 120: 7461

Suche in Google Scholar
13d Rigby JH. Qabar M. J. Org. Chem. 1989, 54: 5853

Suche in Google Scholar
13e Baldwin JE. Adlington RM. Aurelia C. Nageswara Rao I. Marquez R. Pritchard GJ. Org. Lett. 2002, 4: 2125

Suche in Google Scholar
14a Zografos AL. Mitsos CA. Igglessi-Markopoulou O. Org. Lett. 1999, 1: 1953

Suche in Google Scholar
14b Irlapati NR. Baldwin JE. Adlington RM. Pritchard GJ. Org. Lett. 2003, 5: 2351

Suche in Google Scholar
14c McCormick LJ. McKee CT. J. Nat. Prod. 1996, 59: 469

Suche in Google Scholar
14d Sheriha MG. Abouamer K. Elshataiwi ZB. Phytochemistry 1987, 26: 3339

Suche in Google Scholar
15a Takahashi S. Kakinuma N. Uchida K. Hashimoto R. Yanagishima T. Nakagawa A. J. Antibiot. 1998, 51: 596

Suche in Google Scholar
15b Takahashi S. Kakinuma N. Uchida K. Hashimoto R. Yanagishima T. Nakagawa A. J. Antibiot. 1998, 51: 1051

Suche in Google Scholar
16 Nair SK. Samuel R. Asokan CV. Synthesis 2001, 573

Thieme Connect
17 Bi X. Liu Q. Sun S. Liu J. Pan W. Zhao L. Dong D. Synlett 2005, 49

Thieme Connect
18a Kang J. Liang F. Sun S. Liu Q. Bi X. Org. Lett. 2006, 8: 2547

Suche in Google Scholar
18b Mellor JM. Schofield SR. Korn SR. Tetrahedron 1997, 53: 17151

Suche in Google Scholar
19a Kocienski PJ. Pontiroli A. Liu Q. J. Chem. Soc., Perkin Trans. 1 2001, 2356
19b Gill S. Kocienski PJ. Kohler A. Pontiroli A. Liu Q. Chem. Commun. 1996, 1743
20 Bi X. Zhang J. Liu Q. Tan J. Li B. Adv. Synth. Catal. 2007, 349: 2301

Crossref Suche in Google Scholar
For reviews see:
21a Lewandowska E. Tetrahedron 2007, 63: 2107

Suche in Google Scholar
21b Shim JG. Park JC. Cho CS. Shim SC. Yamamoto Y. Chem. Commun. 2002, 852