Ring Transformations of 2-Formylglycals with C,N-Dinucleophiles

Alina Montero; Holger Feist; Manfred Michalik; Jose Quincoces; Klaus Peseke

doi:10.1055/s-2002-23543

Subscribe to RSS

Please copy the URL and add it into your RSS Feed Reader.

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

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2002(5): 0664-0668
DOI: 10.1055/s-2002-23543

PAPER

Ring Transformations of 2-Formylglycals with C,N-Dinucleophiles [1]

Alina Montero^a,b, Holger Feist^a, Manfred Michalik^c, Jose Quincoces^d, Klaus Peseke*^a
^a Universität Rostock, Fachbereich Chemie, Albert-Einstein-Str. 3a, 18051 Rostock, Germany
Fax: +49(381)4986412; e-Mail: klaus.peseke@chemie.uni-rostock.de;
^b Centro de Bioactivos Químicos, Universidad Central de Las Villas, Carretera a Camajuaní, km 5.5. Santa Clara, Cuba
^c Institut für Organische Katalyseforschung, Buchbinderstraße 5-6, 18055 Rostock, Germany
^d Universidade Bandeirante de Sao Paulo, Rua Maria Candida, 1813, Vila Guilherme, São Paulo, CEP: 02071-013, Brazil

Further Information

Publication History

Received 30 November 2001
Publication Date:
02 April 2002 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

The ring transformations of 2-formylglycals with 2-cyano-N-(4-methoxyphenyl)acetamide, 2-benzimidazolylacetonitrile, 2-nitromethylbenzimidazole yielded 5-(1,2,4-tri-O-benzyl-d-arabino/lyxo-1,2,3,4-tetrahydroxybutyl)-1,2-dihydro-1-(4-methoxyphenyl)-2-oxopyridine-3-carbonitriles (2), 2-(1,2,4-tri-O-benzyl-d-arabino/lyxo-1,2,3,4-tetrahydroxybutyl)benzo[4,5]imidazo[1,2-a]pyridine-4-carbonitriles (3) and 2-(1,2,4-tri-O-benzyl-d-lyxo-1,2,3,4-tetrahydroxybutyl)-4-nitrobenzo[4,5]imidazo[1,2-a]pyridine (4), respectively.

Key words

aldehydes - nucleosides - carbohydrates - formylglycals - push-pull alkenes

1

Presented at the XX^th International Carbohydrate Symposium, Hamburg, Germany, 2000.

References

2 Valpuesta Fernández M. López Herrera FJ. Gómez Pérez C. Carbohydr. Res. 1983, 124: 333

Crossref Google Scholar
3 Mancera M. Rodriguez E. Roffé I. Glabis JA. Conde CF. Conde A. Carbohydr. Res. 1991, 210: 327

Crossref Google Scholar
4 Mancera M. Rodriguez E. Roffé I. Glabis JA. Carbohydr. Res. 1994, 253: 307

Crossref Google Scholar
5 Bernal Montes JC. Borrachero Moya P. Cabrera Escribano F. Gómez Guillen M. Madrid Díaz F. Moreno Martínez JM. Carbohydr. Res. 1996, 285: 49

Google Scholar
6 Alahiane A. Rochdi A. Taourirte M. Redwane N. Sebti S. Lazrek HB. Tetrahedron Lett. 2001, 42: 3579

Crossref Google Scholar
7 Schaeffer HJ. Beauchamp L. de Miranda P. Elion GB. Bauer DJ. Collins P. Nature (London) 1978, 272: 583

Crossref Google Scholar
8 Chu CK. Cutle SJ. J. Heterocycl. Chem. 1986, 23: 289

Crossref Google Scholar
9 Remy RJ. Secrist JA. Nucleosides Nucleotides 1985, 4: 411

Google Scholar
10 Kim D.-K. Kim Y.-W. Lee N. J. Heterocycl. Chem. 2001, 38: 45

Crossref Google Scholar
11 Rudloff I. Michalik M. Montero A. Peseke K. Synthesis 2001, 1686

Article in Thieme Connect Google Scholar
12 Ramesh NG. Balasubramanian KK. Tetrahedron Lett. 1991, 32: 3875

Crossref Google Scholar
13 Rudloff I. Peseke K. Reinke H. J. Prakt. Chem. 1998, 340: 334

Crossref Google Scholar
14 Organikum J. A. Barth Verlag; Heidelberg: 1996. p.502

Google Scholar
15 Copeland RAB. Day AR. J. Am. Chem. Soc. 1943, 65: 1072

Crossref Google Scholar
16 Schäfer H. Gewald K. Z. Chem. 1976, 16: 272

Google Scholar
17 Clerc P. Simon S. Tabellen zur Strukturaufklärung organischer Verbindungen mit spektroskopischen Methoden Springer-Verlag; Berlin: 1981. p.C235

Google Scholar
18 Nicotra F. Perego R. Ronchetti F. Russo G. Toma L. Carbohydr. Res. 1984, 131: 180

Crossref Google Scholar
19 Jung ME. Lyster MA. J. Org. Chem. 1977, 42: 3761

Crossref Google Scholar

1

Presented at the XX^th International Carbohydrate Symposium, Hamburg, Germany, 2000.