Triazolopyrimidine

Triazolo[4,5-d]pyrimidine




Reference:
ACS Pharmacol. Transl. Sci. 2025, 8, 1072–1086.

Azauracil

Reference:
J. Med. Chem. 2014, 57, 3912-3923.
The detailed experimental procedures can be found in the freely accessible Supporting Information.

Pyridazinone

Pyridazin-4(1H)-one





Reference:
J. Med. Chem. 2014, 57, 22, 9627-9643.

Benzoimidazopyrimidine

1,4-Dihydrobenzo[4,5]imidazo[1,2-a]pyrimidine

Reference:
J. Med. Chem. 2023, 66, 890-912.

Imidazopyridine

Imidazo[1,2-a]pyridine
Groebke–Blackburn–Bienaymé Multicomponent Reaction





Reference:
Monatsh Chem 2008, 139, 931-933.

4-Pyrone

Reference:
Org. Lett. 2007, 9, 2517-2520.

2-Pyridone

Reference:
J. Med. Chem. 2018, 61, 10206-10217.

4-Pyridone

Route 1

Reference:
Org. Process Res. Dev. 2016, 20, 1461-1468.

Route 2

Reference:
Org. Lett. 2015, 17, 564-567.

The pyridones illustrated in the Routes 1 and 2 are key intermediates used to synthesize dolutegravir and cabotegravir, HIV integrase inhibitors.

Pyrrole

Route 1

---

Paar-Knorr Pyrrole Synthesis





Reference:
J. Med. Chem. 2009, 52, 3377-3384.


Route 2

---

Clauson-Kaas Pyrrole Synthesis






Reference:
J. Med. Chem. 2016, 59, 4511-4525.


Route 3

---

Hantzsch Pyrrole Synthesis




HSVM: High-speed vibration milling

Reference:
Org. Chem. Front. 2014, 1, 458-463.

Pyrazole

Route 1
5-Aminopyrazole




Reference:
J. Agri. Food Chem. 2024, 72, 3334-3341.

Route 2





Reference:
J. Med. Chem. 2018, 61 2552–2570.

Route 3





Reference:
J. Med. Chem. 2024, 67, 18290–18316.

Route 4
5-Hydoxypyrazole

Reference:
J. Med. Chem. 2025, 68, 23375–23388.

Route 5

Reference:
Eur. J. Med. Chem. 2023, 250, 115174.

Route 6

Reference:
Org. Synth. 2008, 85, 179.