Triazolopyrazine Series

Tropic acid (2.0 g, 12 mmol, 1 equiv.) and pTsOH (0.12 g, 0.12 mmol, 0.01 equiv.) were dissolved in EtOH (24 mL) and the reaction mixture was heated to reflux for x h.

Solvent was removed in vacuo to yield a colourless oil.

InChI=1S/C9H10O3/c10-6-8(9(11)12)7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)

to

InChI=1S/C11H14O3/c1-2-14-11(13)10(8-12)9-6-4-3-5-7-9/h3-7,10,12H,2,8H2,1H3

O=C(O)C(CO)C1=CC=CC=C1

to

O=C(OCC)C(CO)C1=CC=CC=C1

Procedure:

AEW 251-1 (200 mg, 0.636 mmol, 1 equiv.), potassium hydroxide (125 mg, 2.22 mmol, 3.5 equiv.) and 18-crown-6 (12 mg, 42.5 μmol, 0.07 equiv.) were stirred in toluene (6.4 mL) and then AEW 261-1 (106 mg, 0.636 mmol, 1 equiv.) was added. The reaction mixture was stirred at room temperature for 30 min.