Allylic azides as potential building blocks for the synthesis of nitrogenated compounds
The synthetic potential of multifunctional allylic azides and imines in attempted intramolecular cyclizations to nitrogen-containing heterocycles was investigated. Tandem Staudinger/aza-Wittig reaction of (E)-3-aryl-2-(azidomethyl)propenoates with triphenylphosphine and aldehydes yielded N-allylic i...
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Sociedade Brasileira de Química
2003-01-01
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| Series: | Journal of the Brazilian Chemical Society |
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| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000600018 |
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doaj-76ef6f0be87c4f51be7ced213e3c2b1f2020-11-25T01:40:24ZengSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society0103-50532003-01-0114610061010Allylic azides as potential building blocks for the synthesis of nitrogenated compoundsSá Marcus M.The synthetic potential of multifunctional allylic azides and imines in attempted intramolecular cyclizations to nitrogen-containing heterocycles was investigated. Tandem Staudinger/aza-Wittig reaction of (E)-3-aryl-2-(azidomethyl)propenoates with triphenylphosphine and aldehydes yielded N-allylic imines in good yield. The (E)-stereochemistry of C=C and C=N bonds was assigned based on NOESY experiments. AlCl3 mediated formation of 3-carbomethoxyquinoline from methyl (E)-2-(azidomethyl)-3-phenylpropenoate is also described.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000600018allylic azides3-carbomethoxyquinolineN-allylic iminesStaudinger/aza-Wittig reactionBaylis-Hillman reaction |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Sá Marcus M. |
| spellingShingle |
Sá Marcus M. Allylic azides as potential building blocks for the synthesis of nitrogenated compounds Journal of the Brazilian Chemical Society allylic azides 3-carbomethoxyquinoline N-allylic imines Staudinger/aza-Wittig reaction Baylis-Hillman reaction |
| author_facet |
Sá Marcus M. |
| author_sort |
Sá Marcus M. |
| title |
Allylic azides as potential building blocks for the synthesis of nitrogenated compounds |
| title_short |
Allylic azides as potential building blocks for the synthesis of nitrogenated compounds |
| title_full |
Allylic azides as potential building blocks for the synthesis of nitrogenated compounds |
| title_fullStr |
Allylic azides as potential building blocks for the synthesis of nitrogenated compounds |
| title_full_unstemmed |
Allylic azides as potential building blocks for the synthesis of nitrogenated compounds |
| title_sort |
allylic azides as potential building blocks for the synthesis of nitrogenated compounds |
| publisher |
Sociedade Brasileira de Química |
| series |
Journal of the Brazilian Chemical Society |
| issn |
0103-5053 |
| publishDate |
2003-01-01 |
| description |
The synthetic potential of multifunctional allylic azides and imines in attempted intramolecular cyclizations to nitrogen-containing heterocycles was investigated. Tandem Staudinger/aza-Wittig reaction of (E)-3-aryl-2-(azidomethyl)propenoates with triphenylphosphine and aldehydes yielded N-allylic imines in good yield. The (E)-stereochemistry of C=C and C=N bonds was assigned based on NOESY experiments. AlCl3 mediated formation of 3-carbomethoxyquinoline from methyl (E)-2-(azidomethyl)-3-phenylpropenoate is also described. |
| topic |
allylic azides 3-carbomethoxyquinoline N-allylic imines Staudinger/aza-Wittig reaction Baylis-Hillman reaction |
| url |
http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000600018 |
| work_keys_str_mv |
AT samarcusm allylicazidesaspotentialbuildingblocksforthesynthesisofnitrogenatedcompounds |
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1725046154311237632 |