Synthesis of New Bis(spiro-β-lactams) via Interaction of Methyl 1-Bromocycloalcanecarboxylates with Zinc and N,N′-Bis(arylmethylidene)benzidines
Interaction of the Reformatsky reagents, prepared from methyl 1-bromocyclopentane-1-carboxylate or methyl 1-bromocyclohexane-1-carboxylate, with N,N′-bis(arylmethylidene)benzidines has given rise to a set of intermediates as a result of nucleophilic addition to the C=N group of a substrate. Further...
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Hindawi Limited
2019-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2019/7496512 |
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doaj-58c32cc6dd464bf3b8df601ab10c41fd2020-11-24T21:14:21ZengHindawi LimitedJournal of Chemistry2090-90632090-90712019-01-01201910.1155/2019/74965127496512Synthesis of New Bis(spiro-β-lactams) via Interaction of Methyl 1-Bromocycloalcanecarboxylates with Zinc and N,N′-Bis(arylmethylidene)benzidinesN. F. Kirillov0E. A. Nikiforova1D. V. Baibarodskikh2T. A. Zakharova3L. S. Govorushkin4Department of Organic Chemistry, Faculty of Chemistry, Perm State University, Perm, RussiaDepartment of Organic Chemistry, Faculty of Chemistry, Perm State University, Perm, RussiaDepartment of Organic Chemistry, Faculty of Chemistry, Perm State University, Perm, RussiaDepartment of Organic Chemistry, Faculty of Chemistry, Perm State University, Perm, RussiaDepartment of Organic Chemistry, Faculty of Chemistry, Perm State University, Perm, RussiaInteraction of the Reformatsky reagents, prepared from methyl 1-bromocyclopentane-1-carboxylate or methyl 1-bromocyclohexane-1-carboxylate, with N,N′-bis(arylmethylidene)benzidines has given rise to a set of intermediates as a result of nucleophilic addition to the C=N group of a substrate. Further intramolecular attack of the amide nitrogen atom onto the ester carbonyl group is responsible for the ring closure, which affords two series of spirocompounds: 2,2′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-2-azaspiro[3.4]octan-1-one) or 2,2′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-2-azaspiro[3.5]nonan-1-ones).http://dx.doi.org/10.1155/2019/7496512 |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
N. F. Kirillov E. A. Nikiforova D. V. Baibarodskikh T. A. Zakharova L. S. Govorushkin |
| spellingShingle |
N. F. Kirillov E. A. Nikiforova D. V. Baibarodskikh T. A. Zakharova L. S. Govorushkin Synthesis of New Bis(spiro-β-lactams) via Interaction of Methyl 1-Bromocycloalcanecarboxylates with Zinc and N,N′-Bis(arylmethylidene)benzidines Journal of Chemistry |
| author_facet |
N. F. Kirillov E. A. Nikiforova D. V. Baibarodskikh T. A. Zakharova L. S. Govorushkin |
| author_sort |
N. F. Kirillov |
| title |
Synthesis of New Bis(spiro-β-lactams) via Interaction of Methyl 1-Bromocycloalcanecarboxylates with Zinc and N,N′-Bis(arylmethylidene)benzidines |
| title_short |
Synthesis of New Bis(spiro-β-lactams) via Interaction of Methyl 1-Bromocycloalcanecarboxylates with Zinc and N,N′-Bis(arylmethylidene)benzidines |
| title_full |
Synthesis of New Bis(spiro-β-lactams) via Interaction of Methyl 1-Bromocycloalcanecarboxylates with Zinc and N,N′-Bis(arylmethylidene)benzidines |
| title_fullStr |
Synthesis of New Bis(spiro-β-lactams) via Interaction of Methyl 1-Bromocycloalcanecarboxylates with Zinc and N,N′-Bis(arylmethylidene)benzidines |
| title_full_unstemmed |
Synthesis of New Bis(spiro-β-lactams) via Interaction of Methyl 1-Bromocycloalcanecarboxylates with Zinc and N,N′-Bis(arylmethylidene)benzidines |
| title_sort |
synthesis of new bis(spiro-β-lactams) via interaction of methyl 1-bromocycloalcanecarboxylates with zinc and n,n′-bis(arylmethylidene)benzidines |
| publisher |
Hindawi Limited |
| series |
Journal of Chemistry |
| issn |
2090-9063 2090-9071 |
| publishDate |
2019-01-01 |
| description |
Interaction of the Reformatsky reagents, prepared from methyl 1-bromocyclopentane-1-carboxylate or methyl 1-bromocyclohexane-1-carboxylate, with N,N′-bis(arylmethylidene)benzidines has given rise to a set of intermediates as a result of nucleophilic addition to the C=N group of a substrate. Further intramolecular attack of the amide nitrogen atom onto the ester carbonyl group is responsible for the ring closure, which affords two series of spirocompounds: 2,2′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-2-azaspiro[3.4]octan-1-one) or 2,2′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-2-azaspiro[3.5]nonan-1-ones). |
| url |
http://dx.doi.org/10.1155/2019/7496512 |
| work_keys_str_mv |
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1716747585420525568 |