Table 1.

Reagents and conditions for synthesis of benzophenones 18–29 and xanthones 30–39.

Entry	Nucleophile	Solvent	Temp (°C)	Time (h)	Yield (%)	Product (reactant)
1	KOH	DMSO/H2O	80	12	92	18 (10)
2	NaOMe	MeOH	26	12	99	19 (10)
3	NH4OH	DMSO/H2O	110c	12	93	20 (10)
4	NH4OH	DMSO/H2O	35	12	75	21 (10)
5	DMF/KOHa	H2O	60	12	78	22 (10)
6	HNEt2	—b	90c	12	85	23 (10)
7	HNEt2	—b	26	12	70	24 (10)
8	H2NiPr	—b	60c	3	93	25 (10)
9	H2NtBu	—b	46	12	82	26 (10)
10	Piperidine	THF	26	12	91	27 (10)
11	Piperidine	THF	26	3	76	28 (10)
12	Morpholine	THF	26	12	81	29 (10)
13	KOH	H2O	200c	3	99	30 (10)
14	KOH	H2O	110	48	99	30 (10)
15	KOH	DMSO/H2O	150c	12	80	31 (21)
16	KOH	DMSO/H2O	150c	12	85	32 (22)
17	KOH	DMSO/H2O	170c	12	85	33 (23)
18	KOH	DMSO/H2O	150c	12	95	34 (24)
19	KOH	DMSO/H2O	150c	16	92	35 (25)
20	KOH	DMSO/H2O	150c	12	90	36 (26)
21	KOH	DMSO/H2O	170c	12	92	37 (27)
22	KOH	DMSO/H2O	150c	12	95	38 (28)
23	KOH	DMSO/H2O	170c	12	83	39 (29)

^aDimethylamine derives from decomposition of DMF.

^bReaction was performed neat.

^cReaction performed in a sealed tube.