Unveiling the Potential of Nonactivated 1,3-Enynes for Controllable Divergent Gold-Catalyzed Cycloaddition with Cyanamides
2026-01-27
SCID: 54.1/7fwxa5ey
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1-aminoisoquinolines2,4-diaminopyrimidines2-aminopyridinesNonactivated 1,3-enynes[2 + 2 + 2]-trimolecular cycloaddition[4 + 2]-bimolecular cycloadditioncyanamideselectronic and steric effectsgold(I)-catalyzed cycloadditionpostmodificationsreaction selectivity
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Abstract (AI)
Nonactivated 1,3-enynes react with cyanamides under gold(I)-catalyzed conditions. This divergent interplay proceeds as [4 + 2]-bimolecular or [2 + 2 + 2]-trimolecular cycloadditions and affords 2-aminopyridines, 1-aminoisoquinolines, and 2,4-diaminopyrimidines. The impact of catalytic systems and electronic/steric parameters on reaction selectivity was studied, and these findings enable directing the cycloaddition along the desired pathway. As a result, a new highly selective modular approach to valuable 2-aminopyridines was proposed. The further synthetic potential of this methodology was demonstrated through postmodifications, including functionalizations of both the heterocyclic backbone and amino substituents.
Key Findings
1
A new highly selective modular approach to synthesize 2-aminopyridines was developed.
2
Catalyst system choice and electronic/steric substrate parameters control reaction selectivity and allow pathway direction.
3
Nonactivated 1,3-enynes react with cyanamides under gold(I) catalysis to undergo divergent cycloadditions.
4
The methodology permits further synthetic elaboration via postmodifications of both the heterocyclic core and amino substituents.
5
The reactions furnish three heterocycle types: 2-aminopyridines, 1-aminoisoquinolines, and 2,4-diaminopyrimidines.
6
Two distinct cycloaddition pathways are accessible: [4+2]-bimolecular and [2+2+2]-trimolecular reactions.
Research Object
Nonactivated 1,3-enynes reacting with cyanamides under gold(I)-catalyzed conditions
Research Subject
Controllable divergent gold-catalyzed cycloaddition pathways ([4+2] bimolecular vs [2+2+2] trimolecular), reaction selectivity modulation by catalytic systems and electronic/steric parameters, and synthesis of 2-aminopyridines, 1-aminoisoquinolines, and 2,4-diaminopyrimidines
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2026-01-27
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