HCID 12677785, compound → Picolinic acid
Reaction equation
O=C1C=C(C(O)=O)OC2C3C=CC=CC=3SCC1=2.COCC1C(=O)C2C[O+](=O)([O-])C3C=CC4CCCCC=4C=3C=2SC=1C(O)=O.O=[C:47]1[CH:52]=[C:51]([C:53]([OH:55])=[O:54])[NH:50][C:49]2C3C4CCCCC=4C=CC=3SC[C:48]1=2>>[N:50]1[CH:49]=[CH:48][CH:47]=[CH:52][C:51]=1[C:53]([OH:55])=[O:54]Participants
Procedure
In the same manner, by using an appropriate amine of formula R16NH2 but replacing 4-oxo-4H,5H-[1]benzothiopyrano[4,3-b]pyran-2-carboxylic acid with an equivalent amount of one of the 4-oxo-tetrahydro-4H,5H-naphtho[2,1-b] or [2,3-b] or [1,2-b]thiopyrano[2,3-d]pyran-2-carboxylic acids (described in Example 79), 4-oxo-1,4,9,10,11,12-hexahydro-5H-naphtho[1',2' : 5,6]thiopyrano[4,3-b]pyridine-2-carboxylic acid (l; R3, R4, R5 and R15 = H, R1 and R2 together form a CH2CH2CH2CH2 chain, X = S and Y = NH), 4-oxo-1,4,8,9,10,11-hexahydro-5H-naphtho[2', 3' : 5,6]thiopyrano]4,3-b]pyridine-2-carboxylic acid (l; R1, R4, R5 and R15 = R2 and R3 together form a CH 2 CH2CH2CH2 chain, X = S and Y = NH), 4-oxo-1,4,7,8,9,10-hexahydro-5H-naphtho[2',1': 5,6]thiopyrano[4,3-b]pyridine-2-carboxylic acid (l; R1, R2, R5 and R15 = H, R3 and R4 together form a CH2CH2CH2CH2 chain, X = S and Y = NH), 1-ethyl-4-oxo-1,4,8,9,10,11-hexahydro-5H-naphtho[2', 3' : 5,6]thiopyrano[4,3-b]pyridine-2-carboxylic acid-6,6-dioxide (l; R1, R4, R5 and R15 = H, R2 and R3 together form a CH2CH2CH2CH2 chain, X = SO2 and Y = NC2H5) and 3-methoxymethyl-4-oxo-1,4,9,10,11,12-hexahydro-5H-naphtho[1', 2' : 5,6]thiopyrano[4,3-b]pyridine-2-carboxylic acid-6,6-dioxide (l; R3, R4 and R15 = H, R1 and R2 together form a CH2CH2CH2CH2 chain, R5 = CH2OCH3, X = SO2 and Y = NH) are obtained, respectively.
Sources & evidence
- ORD record
- ord-09ff0414cbf4401ea3a77dcd92c2cdda
- Source dataset
- uspto-grants-1978_08
- Patent number
- US04105778
Reaction notes
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