. 2018 Mar 16;23(3):674. doi: 10.3390/molecules23030674

Table 1.

Yields for the two-step synthesis of 1-aryl-5-nitro-1H-indazoles.

graphic file with name molecules-23-00674-i001.jpg

Substrate	Ar	Time (h) ^a	Pdt	% Yield ^b
5	a Ph-	2	11a	95
5	b 2-MeOPh-	2	11b	82
5	c 3-MeOPh-	2	11c	81
5	d 4-MeOPh-	2	11d	94
5	e 4-BrPh-	2	11e	95
5	f 3-ClPh-	2	11f	87
5	g 4-ClPh-	2	11g	93
5	h 2,4-Cl₂Ph	36	11h	80
5	I 3-CF₃Ph-	2	11i	88
5	j 4-CF₃Ph-	2	11j	70
5	k 4-CNPh-	2	11k	80
5	l 4-H₂NSO₂Ph-	10	11l	70
5	m 4-HO₂CPh-	24	11m	75
6	a Ph-	2	12a	72
6	b 2-MeOPh-	2	12b	0 ^c
6	c 3-MeOPh-	2	12c	67
6	d 4-MeOPh-	2	12d	70
6	e 4-BrPh-	2	12e	70
6	f 3-ClPh-	2	12f	60
6	g 4-ClPh-	2	12g	70
6	h 2,4-Cl2Ph-	2	12h	60
6	I 3-CF₃Ph-	2	12i	62
6	j 4-CF₃Ph-	2	12j	68
6	k 4-CNPh-	3	12k	60
6	l 4-H₂NSO₂Ph-	2	12l	50
6	m 4-HO₂CPh-	2	12m	50

^a All hydrazones were generated in two hours. Times given are for the final cyclization. ^b Isolated yield of 1H-indazole for the two-step sequence. ^c Only the hydrazone was isolated.