. 2018 Mar 6;14:560–575. doi: 10.3762/bjoc.14.43

Table 1.

Comparison of various conditions applied in the synthesis of amidoalkylnaphthols 4.

entry	R¹	R²	catalyst	conditions	yields (%)	ref.

1	Ph, 2,4-Cl₂Ph, 3-BrPh, 4-NO₂Ph, 4-(CHO)Ph, 5-Br-2-OHPh, 2-pyridyl, 4-MePh, Et, 3-OEt-4-OHPh, 4-OHPh, 4-OMePh, 3-BrPh	Me, Ph, NH₂	ASA NPs	80 °C, 8–30 min	67–96	[19]
2	Ph, 2-ClPh, 4-ClPh, 4-BrPh, 4-MePh, 4-OMePh, 3-NO₂Ph, 4-NO₂Ph, 4-CNPh, 3-OMePh, 1-Nph	Me, NH₂	nano-sulfated zirconia	120 °C, 32–85 min	81–94	[20]
3	Ph, 4-MePh, 4-ClPh, 4-OMePh, 4-NO₂Ph, 3-NO₂Ph, 2-ClPh, 2-NO₂Ph, 2-MePh, 3-OMePh	Me	PbS nanoparticles	120 °C, 4–9 min	85–95	[21]
4	Ph, 4-MePh, 4-NMe₂Ph, 4-OMePh, 3-NO₂Ph, 4-FPh, 2,4-Cl₂Ph, 2,5-(OMe)₂Ph, 3,4-(OMe)₂Ph, 2,3-(OMe)₂Ph, 2-ClPh, 2-NO₂Ph, 3-OH-4-OMePh, 2-FPh, C₁₀H₇, Et, Pr	Me, Ph, NH₂	MNPs–SO₃H	100 °C, 7–35 min	77–97	[22]
5	Ph, 4-NO₂Ph, 4-ClPh, 2,5-(OMe)₂Ph, 2-furyl, 2-thiophene, 1-Nph, 2-Nph, C(Me)=CH-Ph, CH=CH-Ph, Ph-Ph	Me, Ph, NH₂	{[HMIM]C(CN)₃}	rt, 5–30 min	90–96	[23]
6		Me, Ph, NH₂	nano SnO₂	rt, 17–35 min	81–88	[23]
7	Ph, 2-ClPh, 4-ClPh, 2,6-Cl₂Ph, 4-BrPh, 3-NO₂Ph, 4-NO₂Ph, 3-MeOPh, 4-MePh, 2,5-(OMe)₂Ph, 4-CNPh, 4-AcPh	Me, Ph, NH₂	[TEBSA][HSO₄]	120 °C, 10 min	73–91	[24]
8	Ph, 4-ClPh, 4-OMePh, 4-MePh, 2-furyl, 2-thiophene, 3-formylchromone	Me, Ph, NH₂, OEt	EAN	rt, 60 min	85–96	[25]
9	Ph, 3-NO₂Ph, 4-OHPh, 4-OMePh, 2-ClPh, 4-ClPh, 4-NO₂Ph, 4-NMe₂Ph, 3,4,5-(OMe)₃Ph	Me, Ph, NH₂	SILC	100 °C, 7–10 min	80–95	[26]
10	Ph, 2-ClPh, 4-ClPh, 2-OMePh, 4-OMePh, Et, Pr	Me, Ph, NH₂	CFBILs	70 °C, 25–60 min	84–94	[27]
11	Ph, 4-MePh, 4-OMePh, 4-NMe₂Ph, 3-NO₂Ph, 2,4-Cl₂Ph, 2-ClPh, 2-NO₂Ph, 2,3-(OMe)₂Ph, C₁₀H₇, Pr	Me, Ph, NH₂	MNP-IL-OAc	100 °C, 60–210 min	82–97	[28]
12		Me, Ph, NH₂	MNP-IL-OAc	sonication, 10–30 min	90–98	[28]
13	Ph, 4-ClPh, 3-NO₂Ph, 4-BrPh, 4-MePh, 3-NO₂Ph, 2-ClPh, 2,4-Cl₂Ph	Me, Ph, NH₂, NHMe, vinyl	p-TSA	DCE, rt, 9–30 h	83–96	[29]
14		Me, Ph, NH₂, NHMe, vinyl	p-TSA	125 °C, 4–10 h	80–95	[29]
15	Ph, 2,4-Cl₂Ph, 3-OMePh, 3-NO₂Ph, 3,4-(OMe)₂Ph, 4,5-(OMe)₂-2-NO₂Ph, 4-BrPh, 3,4,5-(OMe)₃Ph, 2-pyridyl, 3-indolyl, 2-furyl	Me, Ph, NH₂	montmorillonite K10	125 °C, 30–120 min	65–96	[30]
16	Ph, 3-NO₂Ph, 4-ClPh, 4-BrPh, 4-MePh, 4-FPh, 2-BrPh, 2-MePh, 2-ClPh, 3-BrPh	Me, Ph, NH₂, NHMe, vinyl	Indion-130	110 °C, 6–30 min	81–94	[31]
17	Ph, 4-MePh, 4-ClPh, 3-NO₂Ph, 2-BrPh, 2,4-Cl₂Ph, 1-Nph, Et	Ph, NH₂, NHMe	I₂	DCE, 125 °C, 10–26 h	35–93	[32]
18	Ph, 4-MePh, 4-ClPh, 3-NO₂Ph, 2-BrPh, 2,4-Cl₂Ph, 1-Nph, Et	Ph, NH₂, NHMe	I₂	125 °C, 4–9 h	20–90	[32]
19	Ph, 4-BrPh, 2-ClPh, 4-ClPh, 2,4-Cl₂Ph, 3-OMePh, 3-NO₂Ph, 4-MePh	Me, Ph, NH₂	K₅CoW₁₂O₄₀·3H₂O	125 °C, 2–6 h	74–88	[33]
20		Me, Ph, NH₂	K₅CoW₁₂O₄₀·3H₂O	DCE, rt, 10–24 h	83–92	[33]
21	Ph, 4-BrPh, 2-ClPh, 4-ClPh, 4-FPh, 4-CNPh, 3-OMePh, 3-NO₂Ph, 4-MePh	Me, Ph, NH₂	HClO₄-SiO₂	DCE, 125 °C, 6–8 h	85–92	[34]
22		Me, Ph, NH₂	HClO₄-SiO₂	125 °C, 8–14 min	90–96	[34]
23	Ph, 4-BrPh, 4-ClPh, 4-FPh, 4-MePh 4-NMe₂Ph, 4-NO₂Ph, 4-OMePh, 3-NO₂Ph, 3-FPh, 3-OMePh, 2,4-Cl₂Ph, 2,5-(OMe)₂Ph, 3,4-(OMe)₂Ph, 2-ClPh, 2-NO₂Ph, 2-MePh	Me, Ph	HClO₄-SiO₂	ACN, 85 °C, 20 h	60–88	[35]
24			HClO₄-SiO₂	110 °C, 30–80 min	76–91	[35]
25			HClO₄-SiO₂	MW 450 W, 12–20 min	75–94	[35]
26	Ph, 4-ClPh, 4-FPh, 3-CF₃Ph, 3-NO₂Ph, 4-MePh, 4-EtPh, 4-OHPh, 4-MeOPh, 3-OMe-4-OHPh, Et, iPr	Me, Ph, NH₂, vinyl	HClO₄-SiO₂	125 °C, 5–9 h	68–93	[36]
27	Et, iPr, CH=CHPh, C₅H₁₀, cyclohexyl, 2-pyridyl, Ph, 4-ClPh, 3-OMePh, 4-pyridyl	Me, Bn	SSA	rt, 1.5–2.5 h	79–85	[37]
28	Ph, 4-ClPh, 2-MePh, 2-ClPh, 3-NO₂Ph, 4-FPh, 4-MePh, 4-BrPh, 2-OMePh, 3-OMePh	Me	ClSO₃H	ACN, 85 °C, 3 h	90–98	[38]
29	Ph, 4-MePh, 4-NO₂Ph, 4-NMe₂Ph, 4-ClPh, 4-BrPh, 4-OMePh, 3-NO₂Ph3-FPh, 4-FPh, 2,4-Cl₂Ph, 2,5-(OMe)₂Ph, 2-ClPh, 3-OMePh, 2-NO₂Ph, 2-MePh, 3,4-(OMe)₂Ph	Me	NaHSO₄·H₂O	ACN, 85 °C, 20 h	65–88	[39]
30			NaHSO₄·H₂O	120 °C, 7–40 min	77–94	[39]
31			NaHSO₄·H₂O	MW 800 W, 3–14 min	73–91	[39]
32	Ph, 4-NMe₂Ph, 4-OMePh, 4-ClPh, 4-BrPh, 3-NO₂Ph, 4-FPh, 2,4-Cl₂Ph, 2-ClPh, 3-OMePh, 2-NO₂Ph, 3-OMePh, 2-NO₂Ph, 2-MePh, 3,4-(OMe)₂Ph, 4-MePh, 4-NO₂Ph, 3-FPh, 2,5-(OMe)₂Ph	Me, Ph	Fe(HSO₄)₃	ACN, 85 °C, 20 h	51–74	[40]
33			Fe(HSO₄)₃	85 °C, 25–80 min	74–97	[40]
34			Fe(HSO₄)₃	MW 450 W, 5–14 min	84–96	[40]
35	Ph, 4-OMePh, 4-MePh, 4-ClPh, 3-NO₂Ph, 2-furyl	Me, Ph, NH₂, vinyl, 2-thiophenyl	Sr(OTf)₂	CHCl₃, 60 °C, 8–15 h	80–96	[41]
36	Ph, 4-OMePh, 4-MePh, 4-ClPh, 4-NO₂Ph, 3-NO₂Ph, 2,4-Cl₂Ph, 2-ClPh, 2-MePh	Me, Ph	CuPW	Bu₄NBr, 100 °C, 90 min	74–95	[42]
37		Me, Ph	CuPMo	Bu₄NBr, 100 °C, 90 min	70–93	[42]
38	Ph, 4-ClPh, 4-BrPh, 4-FPh, 4-CNPh, 3-NO₂Ph, 3-OMePh, 2-ClPh	Me, Ph, NH₂	wet-TCT	100 °C, 8–14 min	90–96	[43]
39	Ph, 3-NO₂Ph, 4-ClPh, 2-MePh, 2-ClPh, 4-FPh, 3-NO₂Ph, 4-BrPh, 3-BrPh, 2-BrPh, 2-furyl	Me	sulfamic acid	sonication, 28–30 °C, 10–60 min	55–92	[44]
40		Me	sulfamic acid	sonication, DCE, 28–30 °C, 25–120 min	78–94	[44]
41	Ph, 4-ClPh, 4-OMePh, 3-NO₂Ph, 2-furyl, 2-ClPh, Et	Me, Ph, NH₂, vinyl	I₂	DCE, rt, 8–24 h	30–93	[45]
42	Ph, 4-NO₂Ph, 3-NO₂Ph, 2-NO₂Ph, 4-ClPh, 2-ClPh, 4-OMePh, 2-OMePh, 4-MePh, 2,4-Cl₂Ph, 4-NMe₂Ph	Me, Ph	P₂O₅	60 °C, 5–15 min	80–97	[46]
43	Ph, 4-NO₂Ph, 3-NO₂Ph, 2-NO₂Ph, 4-CN-Ph, 4-FPh, 3-FPh, 4-BrPh, 2-ClPh, 2,4-Cl₂Ph, 4-ClPh, 2-MePh, 4-MePh, 3-OMePh, 4-OMePh, 3,4-(OMe)₂Ph, CH=CH-Ph	Me, Ph	P₂O₅·SiO₂	100 °C, 3–40 min	54–94	[47]
44	Ph, 4-OHPh, 4-ClPh, 2-ClPh, 4-NO₂Ph, 3-NO₂Ph, 4-OMePh, Et, 4-NMe₂Ph, 3,4,5-(OMe)₃Ph	NH₂	TBBDA	rt, 30–80 min	88–97	[48]
45	Ph, 3,4,5,-(OMe)₃Ph, 4-OMePh, 2,3-Me₂Ph, 4-FPh, 4-ClPh, 2-OHPh, 4-NO₂Ph, 2,4-Cl₂Ph, 2-OMePh, 2-ClPh, 2-BrPh, 3-BrPh, 3-FPh, 3-ClPh, 4-(CHO)Ph, Et, 4-CNPh, 4-IPh	Me, Ph	MSI	[Bpy]BF₄, 80 °C, 25–60 min	82–95	[49]
46	Ph, 4-ClPh, 4-OMePh, 4-MePh, 4-NMe₂Ph, 4-NO₂Ph, 2-NO₂Ph, 2-ClPh, 2,4-Cl₂Ph, 4-OH-3-OMePh, 3-OMePh, 3-NO₂Ph, 4-FPh, 2,5-(OMe)₂Ph, 3,4-(OMe)₂Ph, 2-MePh, 4-OHPh, 3-ClPh	Me, Ph, NH₂	succinic acid	120 °C, 3–60 min	65–98	[50]
47	Ph, 4-ClPh, 4-NMe₂Ph, 3-NO₂Ph, 2,5-(OMe)₂	Me, Ph, NH₂	tannic acid	MW 480 W, 5–13 min	85–90	[51]
48			tannic acid	oil bath, 110–120 °C, 7–20 min	75–90	[51]
49			tannic acid	hot plate, 110–120 °C, 10–21 min	47–76	[51]
50	Ph, 4-ClPh, 4-NMe₂Ph, 4-MePh, 3-NO₂Ph, 2,5-(OMe)₂Ph	Me, Ph, NH₂	p-nitrobenzoic acid	MW 450 W, 8–14 min	82–92	[52]
51			p-nitrobenzoic acid	oil bath, 110–120 °C, 12–26 min	80–90	[52]
52			p-nitrobenzoic acid	hot plate, 110–120 °C, 13–32 min	60–74	[52]
53	Ph, 4-BrPh, 2-ClPh, 4-ClPh, 2,4-Cl₂Ph, 4-FPh, 4-OMePh, 4-MePh, 3-NO₂Ph, 4-NO₂Ph	Me	CBSA	130 °C, 2–20 min	86–93	[53]
54	Ph, 4-ClPh, 4-OMe, 4-NO₂Ph, 2-NO₂Ph, 2-ClPh, 4-MePh	Me, Ph, NH₂	citric acid	120 °C, 7–43 min	87–94	[54]
55	Ph, 4-ClPh, 4-NMe₂Ph, 4-MePh, 3-NO₂Ph, 2,5-(OMe)₂Ph, 2-thiophene, 1-Nph, 2-Cl-5-FPh	Me, Ph, NH₂	sulfanilic acid	MW 450 W, 8–14 min	83–94	[55]
56			sulfanilic acid	oil bath, 110–120 °C, 12–24 min	80–95	[55]
57			sulfanilic acid	hot plate, 110–115 °C, 11–28 min	62–72	[55]
58	Ph, 2-NO₂Ph, 3-NO₂Ph, 4-NO₂Ph, 2-ClPh, 4-ClPh, 2,4-Cl₂Ph, 4-MePh, 4-MeOPh, Et, Pr	Me, Ph, NH₂	Bi(NO₃)₃·5H₂O	80 °C, 6–150 min	79–97	[56]
59	Ph, 4-ClPh, 4-BrPh, 3-NO₂Ph, 4-FPh, Et	Me, Ph, NH₂	1-hexanesulfonic acid sodium salt	MW, 3–20 min	35–95	[57]
60	Ph, 4-NO₂Ph, 3-NO₂Ph, 4-OMePh, 4-iPrPh, 2-BrPh, CH₂-CH₂-Ph, CH=CH-Ph, C₁₁H₂₃, 9-phenanthrenyl, 1-pyrenyl	Me, Ph	ZrO(OTf)₂	80 °C, 1.5–10 min	65–98	[58]
61	Ph, 3-NO₂Ph, 4-NO₂Ph, 3-FPh, 4-FPh, 4-OMePh, 2-OMePh	Me, Ph	SO₃H-carbon	100 °C, 30 min	71–96	[59]
62	Ph, 4-ClPh, 4-BrPh, 4-EPh, 4-MePh, 4-OHPh, 3-OHPh, 4-OMePh, 4-OEtPh, 3-NO₂Ph, 2-NO₂Ph, iPr	Me	MCM-41-N-propyl- sulfamic acid	130 °C, 90–270 min	35–98	[60]
63	Ph, 2-ClPh, 4-MePh, 3-NO₂Ph, 2-NO₂Ph, 4-OMePh, 4-BrPh, 4-ClPh	Me, Ph, NH₂, NHMe, vinyl	polyphosphate ester	80 °C, 10–20 min	85–93	[61]
64	Ph, 4-MePh, 2-MePh, 4-OMePh, 3-OMePh, 3,4-(OMe)₂Ph, 4-NMe₂Ph, 4-NO₂Ph, 3-NO₂Ph, 2-NO₂Ph, 4-ClPh, 2-ClPh, 4-BrPh, 4-FPh, 2,4-Cl₂Ph	Me	Amberlite IR-120	MW 360 W, 3–6 min	91–96	[62]