TechnoRep - Faculty of Technology and Metallurgy Repository
University of Belgrade - Faculty of Technology and Metallurgy
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrillic)
    • Serbian (Latin)
  • Login
View Item 
  •   TechnoRep
  • Tehnološko-metalurški fakultet
  • Radovi istraživača / Researchers’ publications (TMF)
  • View Item
  •   TechnoRep
  • Tehnološko-metalurški fakultet
  • Radovi istraživača / Researchers’ publications (TMF)
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

Cyclopropyl building blocks in organic synthesis, part 143. A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives

Authorized Users Only
2007
Authors
Yucel, Baris
Valentić, Nataša
Noltemeyer, Mathias
de Meijere, Armin
Article (Published version)
Metadata
Show full item record
Abstract
A palladium-catalyzed reaction of methylenespiropentane (11) with iodobenzene (12) under typical Heck conditions [Pd(OAC)(2), PPh3, Et3N, DMF] produced a mixture of the unstable [3]dendralene 13 and allylidenecyclopropane 14 in 38 % yield. When an analogous reaction with iodobenzene was carried out in the presence of morpholine (25) and of tris(2-furyl)phosphane (TFP) instead of triphenylphosphane, the dienes 26, 28 and 31 were generated by nucleophilic trapping of pi-allylpalladium intermediates 30 and 32. The cross coupling of methylenespiropentane (11) with the functionalized aryl iodides 33a-g in the presence of a palladium precatalyst [Pd(OAc)2, TFP, Et3N, DMF] at 80 degrees C, 3 h, provided the seven-membered 3,4-dimethylene-substituted heterocycles 34a-g and 35b which, upon addition of dimethyl fumarate (19), underwent Diels-Alder reactions to furnish bicyclic and higher oligocyclic dihydrobenzoxepine and -benzazepine derivatives 36a-g and 37b, yet in rather moderate yields of 1...8-29 % only. The overall process constitutes a one-pot, two-step, three-component queuing cascade. (

Keywords:
pi-allylpalladium species / benzazepine / benzoxepine / bicyclopropylidene / methylenespiropentane
Source:
European Journal of Organic Chemistry, 2007, 2007, 24, 4081-4090
Publisher:
  • Wiley-VCH Verlag Gmbh, Weinheim

DOI: 10.1002/ejoc.200700354

ISSN: 1434-193X

WoS: 000249057500014

Scopus: 2-s2.0-34548083408
[ Google Scholar ]
7
7
URI
http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1171
Collections
  • Radovi istraživača / Researchers’ publications (TMF)
Institution/Community
Tehnološko-metalurški fakultet
TY  - JOUR
AU  - Yucel, Baris
AU  - Valentić, Nataša
AU  - Noltemeyer, Mathias
AU  - de Meijere, Armin
PY  - 2007
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1171
AB  - A palladium-catalyzed reaction of methylenespiropentane (11) with iodobenzene (12) under typical Heck conditions [Pd(OAC)(2), PPh3, Et3N, DMF] produced a mixture of the unstable [3]dendralene 13 and allylidenecyclopropane 14 in 38 % yield. When an analogous reaction with iodobenzene was carried out in the presence of morpholine (25) and of tris(2-furyl)phosphane (TFP) instead of triphenylphosphane, the dienes 26, 28 and 31 were generated by nucleophilic trapping of pi-allylpalladium intermediates 30 and 32. The cross coupling of methylenespiropentane (11) with the functionalized aryl iodides 33a-g in the presence of a palladium precatalyst [Pd(OAc)2, TFP, Et3N, DMF] at 80 degrees C, 3 h, provided the seven-membered 3,4-dimethylene-substituted heterocycles 34a-g and 35b which, upon addition of dimethyl fumarate (19), underwent Diels-Alder reactions to furnish bicyclic and higher oligocyclic dihydrobenzoxepine and -benzazepine derivatives 36a-g and 37b, yet in rather moderate yields of 18-29 % only. The overall process constitutes a one-pot, two-step, three-component queuing cascade. (
PB  - Wiley-VCH Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - Cyclopropyl building blocks in organic synthesis, part 143. A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives
EP  - 4090
IS  - 24
SP  - 4081
VL  - 2007
DO  - 10.1002/ejoc.200700354
UR  - conv_2867
ER  - 
@article{
author = "Yucel, Baris and Valentić, Nataša and Noltemeyer, Mathias and de Meijere, Armin",
year = "2007",
abstract = "A palladium-catalyzed reaction of methylenespiropentane (11) with iodobenzene (12) under typical Heck conditions [Pd(OAC)(2), PPh3, Et3N, DMF] produced a mixture of the unstable [3]dendralene 13 and allylidenecyclopropane 14 in 38 % yield. When an analogous reaction with iodobenzene was carried out in the presence of morpholine (25) and of tris(2-furyl)phosphane (TFP) instead of triphenylphosphane, the dienes 26, 28 and 31 were generated by nucleophilic trapping of pi-allylpalladium intermediates 30 and 32. The cross coupling of methylenespiropentane (11) with the functionalized aryl iodides 33a-g in the presence of a palladium precatalyst [Pd(OAc)2, TFP, Et3N, DMF] at 80 degrees C, 3 h, provided the seven-membered 3,4-dimethylene-substituted heterocycles 34a-g and 35b which, upon addition of dimethyl fumarate (19), underwent Diels-Alder reactions to furnish bicyclic and higher oligocyclic dihydrobenzoxepine and -benzazepine derivatives 36a-g and 37b, yet in rather moderate yields of 18-29 % only. The overall process constitutes a one-pot, two-step, three-component queuing cascade. (",
publisher = "Wiley-VCH Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "Cyclopropyl building blocks in organic synthesis, part 143. A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives",
pages = "4090-4081",
number = "24",
volume = "2007",
doi = "10.1002/ejoc.200700354",
url = "conv_2867"
}
Yucel, B., Valentić, N., Noltemeyer, M.,& de Meijere, A.. (2007). Cyclopropyl building blocks in organic synthesis, part 143. A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives. in European Journal of Organic Chemistry
Wiley-VCH Verlag Gmbh, Weinheim., 2007(24), 4081-4090.
https://doi.org/10.1002/ejoc.200700354
conv_2867
Yucel B, Valentić N, Noltemeyer M, de Meijere A. Cyclopropyl building blocks in organic synthesis, part 143. A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives. in European Journal of Organic Chemistry. 2007;2007(24):4081-4090.
doi:10.1002/ejoc.200700354
conv_2867 .
Yucel, Baris, Valentić, Nataša, Noltemeyer, Mathias, de Meijere, Armin, "Cyclopropyl building blocks in organic synthesis, part 143. A two-step, three-component queuing cascade leading to dihydrobenzoxepine and dihydrobenzazepine derivatives" in European Journal of Organic Chemistry, 2007, no. 24 (2007):4081-4090,
https://doi.org/10.1002/ejoc.200700354 .,
conv_2867 .

DSpace software copyright © 2002-2015  DuraSpace
About TechnoRep | Send Feedback

OpenAIRERCUB
 

 

All of DSpaceInstitutions/communitiesAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About TechnoRep | Send Feedback

OpenAIRERCUB