Ethyl propiolate → 7,7-dimethyl-7,8-dihydroquinoline-2,5(1H,6H)-dione

反応式

[O:1]=[C:2]1CCC[C:8]2NC(=S)C(C#N)=C[C:3]1=2.[NH2:15][C:16]1[CH2:21][C:20]([CH3:23])([CH3:22])[CH2:19][C:18](=[O:24])[CH:17]=1.C(OCC)(=O)C#C>>[CH3:22][C:20]1([CH3:23])[CH2:21][C:16]2[NH:15][C:2](=[O:1])[CH:3]=[CH:8][C:17]=2[C:18](=[O:24])[CH2:19]1

参加物

反応物 3

HCID 12182Ethyl propiolate

HCID 1366803-Amino-5,5-dimethyl-2-cyclohexen-1-one

HCID 18499675-Oxo-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile

生成物 1

HCID 135163797,7-dimethyl-7,8-dihydroquinoline-2,5(1H,6H)-dione収率 78.5%

実験手順

In analogy to (Pettit, G. R.; Fleming, W. C.; Paull, K. D. J. Org. Chem. 1968, 33 (3) 1089-1092), 3-amino-5,5-dimethylcyclohex-2-en-1-one was reacted with ethyl propio-late to give the title compound as a light brown solid in 78.5% yield.

出典と根拠

ORDレコード: ord-43529e555611496dbaf7d858aba485d9
出典データセット: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07598384B2

反応ノート

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