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. 2021 Dec 1;122(1):565–788. doi: 10.1021/acs.chemrev.1c00449

Scheme 216. Synthetic Routes of the Ullazine Derivatives.

Scheme 216

Reagents and conditions: (a)409 (1) 1,4-diphenylbut-2-yne-1,4-dione, DCM, 5 min, rt, (2) DDQ, toluene, rt, 3 h; (b) hydrazine, ethanol, overnight, 80 °C; (c)410 (1) 1,2-naphthoquinone, DCM, TEA, rt, 5 min, (2) DDQ, toluene, rt, 3 h; (d) HOAc, toluene, 100 °C, 72 h; (e)413 Pd(dppf)Cl2, Na2CO3, DMSO, 100 °C, 16 h; (f) PdCl2(PPh3)2, PPh3, K2CO3, DMF/H2O, 90 °C, 24 h; (g) hν (254 nm), decalin, 100 °C, 2 h; (h)411 (1) i-Pr2NEt, CsF, DMSO, 160 °C, 12 h, (2) DDQ, DCM, rt, 20 min; (i) Pd(AcO)2, P(t-Bu)2Me·HBF4, DBU, DMA, 160 °C, 12 h.