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. 2020 Aug 3;16:1881–1900. doi: 10.3762/bjoc.16.156

Table 9.

Green chemistry metrics for the synthesis of dihydropyrimidinones/-thiones 7.

graphic file with name Beilstein_J_Org_Chem-16-1881-i006.jpg

entry reactants product AE (%) E-factora PMIb Curzon’s RMEc (%) gRMEd
(%)

Ar 5/6

1 phenyl: 2a 5 7a 88 45.254 46.254 85 2.2
2 4-methylphenyl: 2b 5 7b 88 43.373 44.373 84 2.3
3 4-methoxyphenyl: 2e 5 7c 89 41.036 42.036 85 2.4
4 3,4-dimethoxyphenyl: 2f 5 7d 90 37.924 38.924 85 2.6
5 3-hydroxyphenyl: 2r 5 7e 89 43.550 44.550 85 2.2
6 2-hydroxyphenyl: 2h 5 7f 89 44.953 45.953 82 2.2
7 4-nitrophenyl: 2l 5 7g 89 39.770 40.770 84 2.5
8 4-fluorophenyl: 2m 5 7h 89 43.220 44.220 85 2.3
9 4-chlorophenyl: 2n 5 7i 89 40.311 41.311 85 2.4
10 3-bromophenyl: 2s 5 7j 90 36.254 37.254 84 2.7
11 2-furanyl: 2p 5 7k 87 50.760 51.760 78 1.9
12 2-thienyl: 2q 5 7l 88 46.600 47.600 81 2.1
13 phenyl: 2a 6 7m 89 43.045 44.045 85 2.3
14 4-methylphenyl: 2b 6 7n 89 41.341 41.341 85 2.4
15 4-methoxyphenyl: 2e 6 7o 90 39.213 40.213 86 2.5
16 4-nitrophenyl: 2l 6 7p 90 37.978 38.978 85 2.6
17 4-chlorophenyl: 2n 6 7q 90 38.685 39.685 86 2.5

aE-factor = minputse − mass of the target product (m7) − mass of the recovered materials/m7. bPMI = (minputs − mass of the recovered materials)/m7 or 1 + E-factor. cCurzon’s RME = m7/m2 + m 4 + m5/6 or yield × AE × 1/SF; SF = 1. dgRME = 100⋅(m7/(minputs − mass of the recovered materials)) or 100⋅(1/(1 + E-factor)). eminputs = m2 + m4 + m5/6 + mS + mC + mWPM + mpurification materials (PM).