Table 1. Tests with Various Bases Required for Heterocyclization of 1 in DMF at Room Temperature.
Yield
of 1a (%)/conversion of 1 (%) |
|||||
---|---|---|---|---|---|
Basea | 0.5 h | 1 h | 1.5 h | 24 h | 96 h |
NaH | 34/54 | 40/62 | 51/72 | 64/90 | – |
K2CO3 | 35/59 | 60/83 | 74/>99 | – | – |
TEA | – | <1/2 | – | 21/27 | 43/50 |
Quinuclidine | 3/5 | 5/8 | 8/10 | 25/30 | – |
DMAP | – | <1/2 | – | 11/19 | 27/36 |
TMG | 90/>99 | 90/>99 | – | – | – |
DBU | 71/83 | 80/95 | – | – | – |
TMGN | 67/89 | 79/98 | – | – | – |
TBD | 73/84 | 75/88 | – | – | – |
P1–H | 80/>99 | 80/>99 | – | – | – |
Structures of all bases are given in Table S1.