HCID 12677785, compound → HCID 86735232, compound
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:46]=[C:47]1[CH:52]=[C:51]([C:53]([OH:55])=[O:54])[NH:50][C:49]2[C:56]3[C:67]4[CH2:66][CH2:65][CH2:64][CH2:63][C:62]=4[CH:61]=[CH:60][C:57]=3[S:58][CH2:59][C:48]1=2>>[O:46]=[C:47]1[CH:52]=[C:51]([C:53]([OH:55])=[O:54])[NH:50][C:49]2[C:56]3[CH:67]=[C:66]4[C:61]([CH2:62][CH2:63][CH2:64][CH2:65]4)=[CH:60][C:57]=3[S:58][CH2:59][C:48]1=2Participants
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 (1;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 (I; R1, R4, R5 and R15 = H, R2 and R3 together form a CH2CH2CH2CH2 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 (I; 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]pyridine2-carboxylic acid-6,6-dioxide (I; R1, R4R5 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 (I; R3, R4 and R 15 = H, R1 and R2 together form a CH2CH2CH2CH2 chain, R5 = CH2OCH3, X = SO2 and Y = NH) are obtained respectively.
Sources & evidence
- ORD record
- ord-870545f756974b43b4676f903c743075
- Source dataset
- uspto-grants-1977_11
- Patent number
- US04060619
Reaction notes
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