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Sulfon-amide
Additional step: activation of carboxy group (COOH into COCl)
SMARTS
: [S;$(S(=O)(=O)[C,N]):1][Cl].[N;$(NC);!$(N=*);!$([N-]);!$(N#*);!$([ND3]);!$([ND4]);!$(N[c,O]);!$(N[C,S]=[S,O,N]):2]>>[S:1][N+0:2]
Conditions
Reactant 1:
sulfonyl chloride.
Reactant 2:
primary or secondary amine.
R1
: C, N.
R2
: alkyl.
R3
: H, alky, aryl.
References
H. Woolven, C. Gonzáles-RodrĂguez, I. Marco, A. L. Thompson, M. C. Willis,
Org. Lett.
,
2011
, 13, 4876-4878.
Other sources
Organic chemistry
Wikipedia