Table 1. Direct addition of alkynes to imines.

Entry	Aldehyde	Aniline	Alkyne	Solvent/temperature, °C/time, days	Yield, %
1	PhCHO	PhNH2	PhCCH	H2O/60/1	91
2	4-CH3C6H4CHO	PhNH2	PhCCH	H2O/60/1	87
3	4-C2H5C6H4CHO	PhNH2	PhCCH	H2O/60/1	86
4	4tBuC6H4CHO	PhNH2	PhCCH	H2O/60/1	86
5	4-ClC6H4CHO	PhNH2	PhCCH	H2O/70/1	90
6	3-ClC6H4CHO	PhNH2	PhCCH	H2O/70/1	89
7	4-BrC6H4CHO	PhNH2	PhCCH	H2O/70/1	95
8	3-BrC6H4CHO	PhNH2	PhCCH	H2O/70/1	93
9	1-NaphCHO	PhNH2	PhCCH	H2O/70/1	96
10	2-NaphCHO	PhNH2	PhCCH	H2O/70/1	75
11	4-PhC6H4CHO	PhNH2	PhCCH	H2O/70/1	85
12	4-CH3OC6H4CHO	PhNH2	PhCCH	H2O/70/1	52
13	4-CF3C6H4CHO	PhNH2	PhCCH	H2O/35/1	87
14	4-NCC6H4CHO	PhNH2	PhCCH	H2O/45/1	40
15	4-O2NC6H4CHO	PhNH2	PhCCH	H2O/45/1	27
16	(CH3)3CCHO	PhNH2	PhCCH	H2O/35/1	64
17	(C2H5)2CHCHO	PhNH2	PhCCH	H2O/45/1	47
18	c-C6H11CHO	PhNH2	PhCCH	H2O/45/1	58
19	PhCHO	4-BrC6H4NH2	PhCCH	Neat/45/1	82
20	PhCHO	4-ClC6H4NH2	PhCCH	Neat/45/1	87
21	PhCHO	4-CH3C6H4NH2	PhCCH	Neat/45/1	77
22	PhCHO	4-CH3OC6H4NH2	PhCCH	Neat/45/1	55
23	PhCHO	PhNH2	HCCH	DMF/22/0.5	78
24	PhCHO	PhNH2	n-C3H7CCH	Neat/45/1	86
25	PhCHO	PhNH2	Et3SiCCH	Toluene/45/1	83
26	PhCHO	PhNH2	Cl(CH2)4CCH	H2O/60/1	57
27	PhCHO	PhNH2	HO(CH2)4CCH	H2O/60/1	80
28	PhCHO	PhNH2	HO(CH2)2CCH	H2O/60/1	82
29	PhCHO	PhNH2	A	H2O/60/1	75

A, 1-Ethynyl-1-cyclohexanol.