S1

Supplementary data

Multicomponent synthesis of new hybrid

PHQ-fatty acids

H. D. Fontecha-Tarazonaa, R. C. Brinkerhoffa, P. M. de Oliveiraa, S. B. Rosaa, D. C. Floresa, C. Da R. Montes D’Ocab, D. Russowskyb and

M. G. Montes D’Oca.*,a

aLaboratório Kolbe de Síntese Orgânica, Escola de Química e Alimentos, Universidade Federal do Rio Grande, Rio Grande, RS, Brazil

bLaboratório de Síntese Orgânica, Instituto de Química, Universidade Federal do Rio Grande do Sul, Porto Alegre, RS, Brazil

Contents

1. Selected 1H and 13C NMR spectra...................................................................S2-S19

*Corresponding author: Escola de Química e Alimentos, Universidade Federal do Rio Grande, Av. Itália, km 08, s/n. Carreiros. 96203-900. Rio Grande, RS, Brazil. Tel: +55 53 32336960; fax +55 53 3233 6961. E-mail address: dqmdoca@furg.br (MGM D’Oca)

Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2015

S2

Figure S1.1H NMR spectrum (CDCl3, 300 MHz) of 12a.

Figure S2.1H NMR spectrum (CDCl3, 300 MHz) of 12b.

NH

O

O

O 12a

NH

O

O

O12b

S3

Figure S3.1H NMR spectrum (CDCl3, 300 MHz) of 12c.

Figure S4.1H NMR spectrum (CDCl3, 300 MHz) of 12d.

NH

O

O

O12c

NH

O

O

O

12d

S4

Figure S5.1H NMR spectrum (CDCl3, 300 MHz) of 12e.

Figure S6.1H NMR spectrum (CDCl3, 300 MHz) of 13a.

NH

O

O

O

OH

13a

NH

O

O

O

OH12e

S5

Figure S7.1H NMR spectrum (CDCl3, 300 MHz) of 13b.

Figure S8.1H NMR spectrum (CDCl3, 300 MHz) of 13c.

NH

O

O

O

OH

13b

NH

O

O

O

OH

13c

S6

Figure S9.1H NMR spectrum (CDCl3, 300 MHz) of 13d.

Figure S10.1H NMR spectrum (CDCl3, 300 MHz) of 13e.

NH

O

O

O

OH

13d

NH

O

O

O

OH

OH13e

S7

Figure S11.1H NMR spectrum (CDCl3, 300 MHz) of 14a.

Figure S12.1H NMR spectrum (CDCl3, 300 MHz) of 14b.

NH

O

O

O14a

OH

NH

O

O

O14b

OH

S8

Figure S13.1H NMR spectrum (CDCl3, 300 MHz) of 14c.

Figure S14.1H NMR spectrum (CDCl3, 300 MHz) of 14d.

NH

O

O

O14c

OH

NH

O

O

O14d

OH

S9

Figure S15. H NMR spectrum (CDCl3, 300 MHz) of 14e.

Figure S16.1H NMR spectrum (CDCl3, 300 MHz) of 15a.

NH

O

O

O

NO2

15a

NH

O

O

O

OH14e

OH

S10

Figure S17.1H NMR spectrum (CDCl3, 300 MHz) of 15b.

Figure S18.1H NMR spectrum (CDCl3, 300 MHz) of 15c.

NH

O

O

O

NO2

15b

NH

O

O

O

NO2

15c

S11

Figure S19.1H NMR spectrum (CDCl3, 300 MHz) of 15d.

Figure S20.1H NMR spectrum (CDCl3, 300 MHz) of 15e.

NH

O

O

O

NO2

15d

NH

O

O

O

NO2

OH15e

S12

Figure S21.1H NMR spectrum (CDCl3, 300 MHz) of 16a.

Figure S22.1H NMR spectrum (CDCl3, 300 MHz) of 16b.

NH

O

O

O

NO2

16a

NH

O

O

O

NO2

16b

S13

Figure S23.1H NMR spectrum (CDCl3, 300 MHz) of 16c.

Figure S24.1H NMR spectrum (CDCl3, 300 MHz) of 16d.

NH

O

O

O

NO2

16c

NH

O

O

O

NO2

16d

S14

Figure S25.1H NMR spectrum (CDCl3, 300 MHz) of 16e.

Figure S26.1H NMR spectrum (CDCl3, 300 MHz) of 17a.

NH

O

O

O

NO2

OH16e

NH

O

O

O17a

Cl

S15

Figure S27.1H NMR spectrum (CDCl3, 300 MHz) of 17b.

Figure S28.1H NMR spectrum (CDCl3, 300 MHz) of 17c.

NH

O

O

O17c

Cl

NH

O

O

O17b

Cl

S16

Figure S29.1H NMR spectrum (CDCl3, 300 MHz) of 17d.

Figure S30.1H NMR spectrum (CDCl3, 300 MHz) of 17e.

NH

O

O

O

OH

17eCl

NH

O

O

O17d

Cl

S17

Figure S31.13C NMR spectrum (CDCl3, 300 MHz) of 12c.

Figure S32.13C NMR spectrum (CDCl3, 300 MHz) of 13b.

NH

O

O

O12c

NH

O

O

O

OH

13b

S18

Figure S33. 13C NMR spectrum (CDCl3, 300 MHz) of 13d.

Figure S34. 13C NMR spectrum (CDCl3, 300 MHz) of 14b.

NH

O

O

O

OH

13d

NH

O

O

O14b

OH

S19

Figure S35.13C NMR spectrum (CDCl3, 300 MHz) of 15e.

Figure S36.13C NMR spectrum (CDCl3, 300 MHz) of 16d.

NH

O

O

O

NO2

OH15e

NH

O

O

O

NO2

16d