Tetrahydroquinolines by multicomponent Povarov reaction in water: Calix[n]arene-catalysed and mechanistic insights
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1 Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 219 Tetrahydroquinolines by multicomponent Povarov reaction in water: Calix[n]arene-catalysed and mechanistic insights Terezinha Ruth Marques Rezende, a Jodieh Oliveira Santana Varejão, a Anna Luísa Lacerda de Almeida Sousa, a Sandra Milena Bonilla Castañeda a and Sergio Antonio Fernandes a, * a Department of Chemistry, CCE, Universidade Federal de Viçosa, Viçosa, MG, , Brazil. santonio@ufv.br or sefernandes@gmail.com Contents 1. EI-MS spectra for compound T1A S1 2. EI-MS spectra for compound T1B S H NMR, 13 C NMR, FT-IR and MS spectra for compound T1 S H NMR and 13 C NMR spectra for compound T1d S H NMR, 13 C NMR, FT-IR and MS spectra for compound T2 S H NMR, 13 C NMR, FT-IR and MS spectra for compound T3 S H NMR, 13 C NMR, FT-IR and MS spectra for compound T4 S H NMR, 13 C NMR, FT-IR and MS spectra for compound T5 S H NMR, 13 C NMR, FT-IR and MS spectra for compound T7 S H NMR, 13 C NMR, FT-IR and MS spectra for compound T8 S H NMR, 13 C NMR, FT-IR and MS spectra for compound T9 S H NMR, 13 C NMR, FT-IR and MS spectra for compound T1 S H NMR, 13 C NMR, FT-IR and MS spectra for compound T11 S H NMR, 13 C NMR, FT-IR and MS spectra for compound T12 S H NMR, 13 C NMR, FT-IR and MS spectra for compound T13 S H NMR, 13 C NMR, FT-IR and MS spectra for compound T15 S H NMR, 13 C NMR, FT-IR and MS spectra for compound T16 S H NMR, 13 C NMR, FT-IR and MS spectra for compound T17 S H NMR, 13 C NMR, FT-IR and MS spectra for compound T18 S H NMR, 13 C NMR, FT-IR and MS spectra for compound T19 S37 S1
2 Compound T1A T1A Relative Intensity ()/m/z Relative Intensity ()/m/z S2
3 Compound T1B T1B Relative Intensity ()/m/z Relative Intensity ()/m/z S3
4 Compound T T1, 1 H NMR, OCDCl 3, 3 MHz Br N H OH ppm S4
5 T1, 13 C NMR, CDCl 3, MHz ppm T1, FT-IR (ATR) S5
6 Relative Intensity ()/m/z Compound T1d T1d, 1 H NMR, CDCl 3, 3 MHz f1 (ppm) S6
7 T1d, 13 C NMR, CDCl 3, MHz f1 (ppm) Compound T2 S7
8 T2, 1 H NMR, CDCl 3, 3 MHz f1 (ppm) T2, 13 C NMR, CDCl 3, MHz f1 (ppm) S8
9 T2, FT-IR (ATR) Relative Intensity ()/m/z S9
10 Compound T T3, 1 H NMR, CDCl 3, 3 MHz f1 (ppm) T3, 13 C NMR, CDCl 3, MHz f1 (ppm) S1
11 T3, FT-IR (ATR) Relative Intensity ()/m/z S11
12 Compound T T4, 1 H NMR, CDCl 3, 3 MHz f1 (ppm) S12
13 T4, 13 C NMR, CDCl 3, MHz f1 (ppm) T4, FT-IR (ATR) S13
14 Relative Intensity ()/m/z Compound T5 T5, 1 H NMR, CDCl 3, 3 MHz S14
15 S f1 (ppm) ppm T5, 13 C NMR, CDCl 3, MHz
16 T5, FT-IR (ATR) Relative Intensity ()/m/z S16
17 Compound T T7a and b, 1 H NMR, CDCl 3, 3 MHz ppm T7a and b, 13 C NMR, CDCl 3, MHz ppm S17
18 NO 2 O O N H OH O 2 N T7a,b, FT-IR (ATR) N H OH Relative Intensity ()/m/z Relative Intensity ()/m/z S18
19 Compound T T8, 1 H NMR, CDCl 3, 6 MHz f1 (ppm) T8, 13 C NMR, CDCl 3, 1 MHz f1 (ppm) S19
20 T8, FT-IR (ATR) Relative Intensity ()/m/z S2
21 S21 Compound T ppm ppm T9, 1 H NMR, CDCl 3, 3 MHz T9, 13 C NMR, CDCl 3, MHz
22 T9, FT-IR (ATR) Relative Intensity ()/m/z S22
23 Compound T T1a and b, 1 H NMR, CDCl 3, 3 MHz f1 (ppm) T1a and b, 13 C NMR, CDCl 3, MHz f1 (ppm) S23
24 T1a.b, FT-IR (ATR) Relative Intensity ()/m/z Relative Intensity ()/m/z S24
25 Compound T T11, 1 H NMR, CDCl 3, 3 MHz ppm T11, 13 C NMR, CDCl 3, MHz ppm S
26 T11, FT-IR (ATR) Relative Intensity ()/m/z S26
27 Compound T T12a and b, 1 H NMR, CDCl 3, 6 MHz f1 (ppm) T12a and b, 13 C NMR, CDCl 3, 1 MHz f1 (ppm) S27
28 T12a,b, FT-IR (ATR) Relative Intensity ()/m/z S28
29 Compound T T13, 1 H NMR, CDCl 3, 3 MHz f1 (ppm) T14, 13 C NMR, CDCl 3, MHz f1 (ppm) S29
30 T13, FT-IR (ATR) Relative Intensity ()/m/z S3
31 Compound T T15, 1 H NMR, CDCl 3, 3 MHz ppm T15, 13 C NMR, CDCl 3, MHz ppm S31
32 T15, FT-IR (ATR) Relative Intensity ()/m/z S32
33 Compound T T16, 1 H NMR, CDCl 3, 3 MHz ppm T16, 13 C NMR, CDCl 3, MHz ppm S33
34 T16, FT-IR (ATR) Relative Intensity ()/m/z S34
35 Compound T T17, 1 H NMR, CDCl 3, 3 MHz ppm T17, 13 C NMR, CDCl 3, MHz ppm S35
36 T17, FT-IR (ATR) Relative Intensity ()/m/z S36
37 Compound T T18, 1 H NMR, CDCl 3, 3 MHz ppm T18, 13 C NMR, CDCl 3, MHz ppm S37
38 T18, FT-IR (ATR) Relative Intensity ()/m/z S38
39 Compound T T19, 1 H NMR, CDCl 3, 3 MHz ppm T19, 13 C NMR, CDCl 3, MHz ppm S39
40 T19, FT-IR (ATR) Relative Intensity ()/m/z S4
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