2024-03-28T13:23:10Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/1325682019-11-12T14:22:14Zcom_10261_48com_10261_5col_10261_301
2016-05-24T09:58:28Z
urn:hdl:10261/132568
Reactivity control in the addition of N,N′-dialkylated 1,n-diamines to activated skipped diynes: Synthesis of fused bicyclic 1,4-diazepanes and 1,5-diazocanes
López-Tosco, Sara
Tejedor, David
González-Platas, Javier
García-Tellado, Fernando
Ministerio de Ciencia e Innovación (España)
European Commission
Fundación Canaria de Investigación Sanitaria
Instituto de Salud Carlos III
Michael addition
Fused-ring systems
Domino reactions
Through-space interactions
Heterocycles
A metal-free domino reaction for the synthesis of a new family of fused bicyclic 1,4-diazepanes and 1,5-diazocanes has been developed. The reaction involves the use of N,N′-dialkylated 1,n-diamines as the nitrogen source, through-space orbital interactions between the two nitrogen atoms as the reactivity director element, and an activated skipped diyne as the reactive platform. A key Morita-Baylis-Hillman-like reaction allows the formation of 1,4-diazepanes and 1,5-diazocanes (medium-sized diazoheterocycles). These structures incorporate a 1,n-diazocycle fused to a Î3-butenolide ring and different functionalities to be used as convenient handles for further complexity generation. The good efficiency of this reaction and its simple experimental protocol make this process an excellent candidate for the fast construction of structure-focused libraries based on this fused bicyclic motif. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
2016-05-24T09:58:28Z
2016-05-24T09:58:28Z
2011-10-19
2016-05-24T09:58:28Z
artículo
European Journal of Organic Chemistry: 6847-6850 (2011)
http://hdl.handle.net/10261/132568
10.1002/ejoc.201101368
http://dx.doi.org/10.13039/501100004837
http://dx.doi.org/10.13039/501100000780
http://dx.doi.org/10.13039/501100004587
eng
Postprint
http://dx.doi.org/10.1002/ejoc.201101368
Sí
closedAccess
John Wiley & Sons