Screening of cyclization conditions to generate 19a.
![]() | |||||
---|---|---|---|---|---|
Entry | Reagent | Solvent | Temperature (°C) | 19 : 32 | Yield (%) |
1 | BDSB | EtNO2 | −78 | 4.9 : 1 | ∼30 b.r.s.m. |
2 | BDSB | MeNO2 | −20 | 5.3 : 1 | ∼30 b.r.s.m. |
3 | BDSB | MeNO2 | 0 | 1.3 : 1 | 20% |
4 | BDSB | CH2Cl2 | −20 | N/A | <10% conv. |
5 | BDSB | CH2Cl2 | 0 | 7.0 : 1 | 49% |
6 | NBS, morpholine | HFIP | 0 to reflux | N/A | N.R. |
Reactions were performed using 0.06 mmol of 23; all reactions using BDSB were conducted for 10 min total.