Optimization of one-pot synthesis of naphthopyranopyrimidine 4a.
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|---|---|---|---|---|
| Entry | Catalyst (mol%) | T (°C) | Time (min) | Yielda (%) |
| 1 | — | 100 | 300 | 0 |
| 2 | ZnCl2 (2) | 100 | 45 | 30 |
| 3 | AlCl3 (2) | 100 | 45 | 60 |
| 4 | FeCl3 (2) | 100 | 45 | 30 |
| 5 | BiCl3 (2) | 100 | 45 | 30 |
| 6 | MnCl2 (2) | 100 | 45 | 20 |
| 7 | p-TSA (2) | 100 | 45 | 50 |
| 8 | NaHSO4 (2) | 100 | 45 | 35 |
| 9 | HNT (2) | 100 | 45 | 30 |
| 10 | [(PATDBP)Cl2@HNT] (2) | 100 | 45 | 45 |
| 11 | [(PATDBP)(HSO4)2@HNT] (2) | 100 | 45 | 98 |
| 12 | [(PATDBP)(HSO4)2@HNT] (1) | 100 | 45 | 70 |
| 13 | [(PATDBP)(HSO4)2@HNT] (4) | 100 | 45 | 98 |
| 14 | [(PATDBP)(HSO4)2@HNT] (2) | 25 | 45 | 10 |
| 15 | [(PATDBP)(HSO4)2@HNT] (2) | 70 | 45 | 50 |
| 16 | [(PATDBP)(HSO4)2@HNT] (2) | 120 | 45 | 98 |
Isolated yields.