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. Author manuscript; available in PMC: 2014 Mar 11.
Published in final edited form as: Chem Commun (Camb). 2013 Mar 11;49(20):2064–2066. doi: 10.1039/c3cc38961h

Table 1.

MannichMCR between pyrrole, paraformaldehyde and aniline under various conditionsa

graphic file with name nihms444939t1.jpg
Entry Catalyst Ratio of 4a/5/2
%b 		Isolated yield
%
1 HOAc (20 mol%) 52//22/26
2 TFA (20 mol%) NA
3 Proline (20 mol%) 7/0/93
4 PTSA (20 mol%) 21/5/74
5 PhCO2H(20 mol%) 28/13/59
6 2 M HCl (20 mol%) 26/4/70
7 MeOCH2CO2H (20 mol%) 45/36/19
8 (3,5-(CF3)2-PhNH)2CS (20 mol%) no reaction
9 HOAc (100 mol%) 59//17/24
10c HOAc (100 mol%) 45/9/46 85 (4a)e
11d MeOCH2CO2H (100 mol%) 0/100/0 75 (5)
a

the reaction was carried out at rt for 24 h in 1 mL CH2Cl2 with 2 (0.1mmol), paraformaldehyde (0.12mmol), aniline (0.12mmol);

b

the ratio is based on UV absorption in LC-MS studies of crude reaction mixture.

c

2 equiv. of pyrrole, 2 equiv. of paraformaldehyde, and 1 equiv. of aniline, were used.

d

1 equiv. of pyrrole, 3 equiv. of formaldehyde, and 3 equiv. of aniline were used, reaction time was 48 h.

e

based on 1 equiv. aniline