An effective contribution to functionalized pyridines synthesis by way of an unusual rearrangement of amidines

被引：7

作者：

Beccalli, EM

Contini, A

Trimarco, P

机构：

[1] Univ Milan, Ist Chim Organ, Fac Farm, I-20133 Milan, Italy

[2] Univ Milan, Ctr Interuniv Ric Reaz Pericicil & Sintesi Sistem, I-20133 Milan, Italy

来源：

TETRAHEDRON | 2002年 / 58卷 / 06期

关键词：

amidines; 2H-pyran-2-one; 2-pyridineacetamide; thermal rearrangement;

D O I：

10.1016/S0040-4020(01)01197-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new synthesis of 2-pyridineacetamides was developed starting from pyran-2-one N-functionalized amidines 4. Secondary amines reacted in a sealed tube with amidines 4 and, by nucleophilic attack on pyran-2-one nucleus and thermal rearrangement, afforded exclusively the 2-pyridineacetamide derivatives 6 or a mixture of amide compounds 6 and 7 depending on the substituents linked to C-alpha of the starting amidine 4. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：1213 / 1221

页数：9

共 23 条

[1] v-triazolines .37. Rearrangement reactions of 5-amino-1-(2-formyl-, -benzoyl-, -cyano-aryl)-v-triazolines: New synthesis of 2-amino- and 2,4-diamino-quinolines and 2,4-diamino-1,7-naphthyridines
Beccalli, EM
Erba, E
Gelmi, ML
Pocar, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (12): : 1359 - 1364
[2] SYNTHESIS AND ANTI-ARRHYTHMIC ACTIVITY OF NEW [(DIALKYLAMINO)ALKYL]PYRIDYLACETAMIDES
BERNHART, CA
CONDAMINE, C
DEMARNE, H
RONCUCCI, R
GAGNOL, JP
GAUTIER, PJ
SERRE, MA
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (03) : 451 - 455
[3] Boyd G. V., 1991, CHEM AMIDINES IMIDAT, V2, P367
[4] BROEKHOF NLJ, 1979, TETRAHEDRON LETT, V26, P2433
[5] 4-AMINO-6-METHYL-2H-PYRAN-2-ONE - PREPARATION AND REACTIONS WITH AROMATIC-ALDEHYDES
CERVERA, M
MORENOMANAS, M
PLEIXATS, R
[J]. TETRAHEDRON, 1990, 46 (23) : 7885 - 7892
[6] CRISPI G, 1982, SYNTHESIS-STUTTGART, P787
[7] Ellis G.P., 1984, Comprehensive Heterocyclic Chemistry, V3, P681
[8] ELLIS GP, 1984, COMPREHENSIVE HETERO, P684
[9] nu-triazolines .38. New synthesis of 4-aminoquinazolines and 6-aminopurines
Erba, E
Sporchia, D
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (20): : 3021 - 3024
[10] v-Triazolines.: Part 42.: Study on the reactivity of 4,5-dihydro-1-(6-methyl-2-oxo-2H-pyran-4-yl)-5-morpholino-v-triazoles.: Synthetic approach to pyrano[4,3-b]pyrrol-4(1H)-ones
Erba, E
Pocar, D
Trimarco, P
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (14): : 1723 - 1728

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