Table 10.

Green chemistry metrics for the synthesis of 2-amino-4-(hetero)aryl-3,5-dicarbonitrile-6-sulfanylpyridines 11.

entry	reactants		product	AE (%)	E-factora	PMIb	Curzon’s RMEc (%)	gRMEd (%)
	Ar	R
1	phenyl: 2a	pyridyl: 9	11a	94	36.054	37.054	90	2.7
2	4-methoxyphenyl: 2e	pyridyl: 9	11b	95	33.026.	34.026	91	2.9
3	3,4,5-trimethoxyphenyl: 2g	pyridyl: 9	11c	95	29.647	30.647	87	3.3
4	3-hydroxyphenyl: 2r	pyridyl: 9	11d	95	35.188	36.188	89	2.8
5	4-nitrophenyl: 2l	pyridyl: 9	11e	95	31.741	32.741	91	3.1
6	4-fluorophenyl: 2m	pyridyl: 9	11f	95	34.356	35.356	90	2.8
7	4-bromophenyl: 2o	pyridyl: 9	11g	95	29.698	30.698	89	3.3
8	3,4-difluorophenyl: 2t	pyridyl: 9	11h	95	34.699	35.699	86	2.8
9	pyridyl: 2u	pyridyl: 9	11i	94	37.143	38.143	87	2.6
10	Phenyl: 2a	phenyl: 10	11j	94	35.474	36.474	92	2.7
11	4-methylphenyl: 2b	phenyl: 10	11k	95	33.991	34.991	93	2.9
12	4-methoxyphenyl: 2e	phenyl: 10	11l	95	32.827	33.827	92	3.0
13	3,4,5-trimethoxyphenyl: 2g	phenyl: 10	11m	95	29.020	30.020	89	3.3
14	4-nitrophenyl: 2l	phenyl: 10	11n	95	32.021	33.021	90	3.0
15	4-fluorophenyl: 2m	phenyl: 10	11o	95	34.319	35.319	91	2.8
16	4-chlorophenyl: 2n	phenyl: 10	11p	95	32.744	33.744	91	3.0
17	3-bromophenyl: 2s	phenyl: 10	11q	95	29.775	30.775	89	3.2
18	pyridyl: 2u	phenyl: 10	11r	94	36.893	37.893	88	2.6

^aE-factor = ^minputs^f − mass of the target product (^m11) − mass of the recovered materials/^m11. ^bPMI = (^minputs − mass of the recovered materials)/^m11 or 1 + E-factor. ^cCurzon’s RME = ^m11/ ^m2 + ^m8 + ^m9/10 or yield × AE × 1/SF; SF = 1. ^dgRME = 100⋅(^m11/(^minputs − mass of the recovered materials)) or 100⋅(1/(1 + E-factor)). ^eminputs = ^m2 + ^m8 + ^m9/10 + ^mS + ^mC + ^mWPM + ^mPM.