Methyl propiolate → 6,7,8,9,9a,10-hexahydrobenzo[g]quinoline-2,5(1H,5aH)-dione

HRID 1817810Notes

Reaction equation

HRID 1817810 reaction equation
[O:1]=[C:2]1CCC[C:8]2NC(=S)C(C#N)=C[C:3]1=2.[NH2:15][C:16]1[CH2:25][CH:24]2[CH:19]([CH2:20][CH2:21][CH2:22][CH2:23]2)[C:18](=[O:26])[CH:17]=1.C(OC)(=O)C#C>>[NH:15]1[C:16]2[CH2:25][CH:24]3[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]3[C:18](=[O:26])[C:17]=2[CH:8]=[CH:3][C:2]1=[O:1]

Participants

4

Reactant 3

HCID 13536Methyl propiolateHCID 18499675-Oxo-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrileHCID 578833273-Amino-4a,5,6,7,8,8a-hexahydro-4H-naphthalen-1-one

Product 1

HCID 578832706,7,8,9,9a,10-hexahydrobenzo[g]quinoline-2,5(1H,5aH)-dione

Procedure

In close analogy to (Pettit, G. R.; Fleming, W. C.; Paull, K. D. J. Org. Chem. 1968, 33 (3) 1089-1092), 3-amino-4a,5,6,7,8,8a-hexahydro-4H-naphthalen-1-one was reacted with methyl propiolate to give the title compound as a colorless solid.

Sources & evidence

ORD record
ord-0b07600102b44f55a31d3e78bbcf28ef
Source dataset
uspto-grants-2009_10
Patent number
US07598384B2

Reaction notes

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