PMID- 15844975
OWN - NLM
STAT- PubMed-not-MEDLINE
DCOM- 20050524
LR  - 20050422
IS  - 0022-3263 (Print)
IS  - 0022-3263 (Linking)
VI  - 70
IP  - 9
DP  - 2005 Apr 29
TI  - Reaction of 2-methoxy-3H-azepine with NBS: efficient synthesis of 2-substituted 
      2H-azepines.
PG  - 3425-36
AB  - [reaction: see text] The reaction of 2-methoxy-3H-azepines, in the presence or 
      absence of a nucleophile, with N-bromosuccinimide (NBS) gave a regioselective 
      1,4-adduct from which the corresponding 2H-azepine derivatives were formed via 
      base-promoted hydrogen bromide elimination, generally in moderate to quantitative 
      yield. Competitive formation of 4-bromo-2-methoxy-3H-azepine by electrophilic 
      substitutuion or 3H-azepin-2-yl 2H-azepin-2-yl ether by transetherification was 
      minimized at lower reaction temperatures. Quantitative substitution of 
      2-(2',4',6'-trichlorophenoxy)-2H-azepine derivatives, formed in moderate yield 
      from the respective 3H-azepine and NBS in the presence of 2,4,6-trichlorophenol 
      (TCP), by various nucleophiles gave the corresponding 2-substituted 2H-azepine. 
      Among these nucleophiles were alkanethiol and alkylamine that are not tolerated 
      in the reaction of 3H-azepine and NBS.
FAU - Cordonier, Christopher E J
AU  - Cordonier CE
AD  - Department of Chemistry, Faculty of Science, Okayama University, Tsushima-Naka 
      3-1-1, Okayama 700-8530, Japan.
FAU - Satake, Kyosuke
AU  - Satake K
FAU - Atarashi, Mikihiko
AU  - Atarashi M
FAU - Kawamoto, Yousuke
AU  - Kawamoto Y
FAU - Okamoto, Hideki
AU  - Okamoto H
FAU - Kimura, Masaru
AU  - Kimura M
LA  - eng
PT  - Journal Article
PL  - United States
TA  - J Org Chem
JT  - The Journal of organic chemistry
JID - 2985193R
EDAT- 2005/04/23 09:00
MHDA- 2005/04/23 09:01
CRDT- 2005/04/23 09:00
PHST- 2005/04/23 09:00 [pubmed]
PHST- 2005/04/23 09:01 [medline]
PHST- 2005/04/23 09:00 [entrez]
AID - 10.1021/jo0500232 [doi]
PST - ppublish
SO  - J Org Chem. 2005 Apr 29;70(9):3425-36. doi: 10.1021/jo0500232.