Dihydrobenzoimidazopyrimidine

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

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

Imidazopyridine

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





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

4-Pyrone

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

2-Pyridone

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

4-Pyridone

Route 1

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

Route 2

Reference:
1.    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

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Paar-Knorr Pyrrole Synthesis





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


Route 2

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Clauson-Kaas Pyrrole Synthesis






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


Route 3

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Hantzsch Pyrrole Synthesis




HSVM: High-speed vibration milling

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

Pyrazole

Route 1

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


Route 2

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

Barbituric Acid (Pyrimidinetrione)

Barbituric Acid (Pyrimidine-2,4,6(1H,3H,5H)-trione)





Reference:
1.    J. Med. Chem. 2016, 59, 2648-2659.

Pyrrolo[1,2-a]quinoxalin-4(5H)-one

Route 1

Reference:
1.    Biorg. Chem. 2022, 126, 105860.

Route 2

Reference:
1.    J. Med. Chem. 2004, 47, 1997-2009.

Route 3

Reference:
1.    J. Med. Chem. 1997, 40, 3670-3678.

Pyrrolo[1,2-a]quinoxaline

Pyrroloquinoxaline

Reference:
1.    Eur. J. Med. Chem. 2013, 65, 205-222.