TY - JOUR
T1 - Polycyclic n-heterocyclic compounds, part 68
T2 - Reactions of 3-(2-bromoethyl)quinazolin-4(3H)-one and 3-(2-bromoethyl)-5,6,7,8- tetrahydroquinazolin-4(3H)-one with primary alkylamines via a dimroth-type rearrangement
AU - Okuda, Kensuke
AU - Ohtomo, Hiromi
AU - Tagata, Tsuyoshi
AU - Hirota, Takashi
AU - Sasaki, Kenji
PY - 2011/1
Y1 - 2011/1
N2 - The reaction of 3-(2-bromoethyl)quinazolin-4(3H)-one with ethyl- and n-propylamine gave abnormal fused 3-alkyl-4-alkyliminoquinazolines via a Dimroth-type rearrangement, as well as normal substituted 3-(2-alkylaminoethyl) derivatives in methanol. The reaction of 3-(2-bromoethyl)-5,6,7,8- tetrahydroquinazolin-4(3H)-one with primary alkylamines was also investigated for the scope of this rearrangement reaction.
AB - The reaction of 3-(2-bromoethyl)quinazolin-4(3H)-one with ethyl- and n-propylamine gave abnormal fused 3-alkyl-4-alkyliminoquinazolines via a Dimroth-type rearrangement, as well as normal substituted 3-(2-alkylaminoethyl) derivatives in methanol. The reaction of 3-(2-bromoethyl)-5,6,7,8- tetrahydroquinazolin-4(3H)-one with primary alkylamines was also investigated for the scope of this rearrangement reaction.
KW - 3-Alkyl-4-alkyliminopyrimidines
KW - Dimroth rearrangement
KW - nucleophilic aromatic substitution
KW - primary alkylamines
KW - pyrimidin-4(3H)-ones
KW - tandem reactions
UR - http://www.scopus.com/inward/record.url?scp=79952075439&partnerID=8YFLogxK
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U2 - 10.1080/00397911003668570
DO - 10.1080/00397911003668570
M3 - Article
AN - SCOPUS:79952075439
SN - 0039-7911
VL - 41
SP - 812
EP - 819
JO - Synthetic Communications
JF - Synthetic Communications
IS - 6
ER -