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Synthesis and isomerization of N-alpha-aza-heteroaryl-beta-lactams
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Troisi, Luigino, Ronzini, Ludovico, Granito, Catia, Pindinelli, Emanuela, Troisi, Alessandro and Pilati, Tullio (2006) Synthesis and isomerization of N-alpha-aza-heteroaryl-beta-lactams. TETRAHEDRON, 62 (51). pp. 12064-12070. doi:10.1016/j.tet.2006.09.075 ISSN 0040-4020.
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Official URL: http://dx.doi.org/10.1016/j.tet.2006.09.075
Abstract
The [2+2] carbonylative cycloaddition of N-cx-aza-heteroaryl substituted imines with allyl bromide led partially to beta-lactams, which underwent isomerization to the more stable alpha,beta-unsaturated carbonyl compound. Pyrimidinone derivatives together with doubly unsaturated amides represent the remaining isolated products. The strong electron-withdrawing effect of the two alpha-aza-heterocycles linked to the nitrogen atom and to the C4 of the 2-azetidinone structure could give a ring expansion, through a 2-azetinone intermediate that affords the pyrimidinone compounds. The substituted amides, instead, should result from a ring-opening reaction of the beta-lactam. (c) 2006 Elsevier Ltd. All rights reserved.
Item Type: | Journal Article | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | TETRAHEDRON | ||||
Publisher: | PERGAMON-ELSEVIER SCIENCE LTD | ||||
ISSN: | 0040-4020 | ||||
Official Date: | 18 December 2006 | ||||
Dates: |
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Volume: | 62 | ||||
Number: | 51 | ||||
Number of Pages: | 7 | ||||
Page Range: | pp. 12064-12070 | ||||
DOI: | 10.1016/j.tet.2006.09.075 | ||||
Publication Status: | Published |
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