A Catalyst-Free Transamination of (E)-N,N-Dimethyl Enaminones to β-Amino-α,β-Unsaturated Carbonyl Compounds by Using Isothiocyanates as Amines Proxy

Abstract

A facile synthesis of β-amino-α,β-unsaturated carbonyl compounds has been accomplished by the reaction of (E)-N,N-dimethyl enaminones with isothiocyanates under metal-, catalyst-, base-, and additive-free conditions. The reaction is straightforward and offers transamination with good substrate scope and functional group tolerance. Notably, the aryl isothiocyanates serve both as an amine surrogate as well as an activating agent.

Keywords

Transamination - Catalyst-free - Aryl isothiocyanates

Publication History

Received: 25 June 2025

Accepted after revision: 14 September 2025

Accepted Manuscript online:
14 September 2025

Article published online:
13 November 2025

• References

• 1a Vreese RD, Grootaert C, D’hoore S. et al. Eur J Med Chem 2016; 123: 727
• 1b Scott KR, Edafiogho IO, Richardson EL. et al. J Med Chem 1993; 36: 1947
• 1c Ahmed EA. J Mex Chem Soc 2015; 59: 181
• 1d Theppawong A, Vreese RD, Vannecke L, Grootaert C, Camp JV, D’hooghe M. Bioorg Med Chem Lett 2016; 26: 5650
• 1e Ghoneima OM, Billa A, Dhugurua J, Szollosi DE, Edafiogho IO. Bioorg Med Chem 2018; 26: 3890
• 2a Noole A, Borissova M, Lopp M, Kanger T. J Org Chem 2011; 76: 1538
• 2b Wan J-P, Loh CCJ, Pan F, Enders D. Chem Commun 2012; 48: 10049
• 2c Wang C, Dong C, Kong L, Li Y, Li Y. Chem Commun 2014; 50: 2164
• 2d Afsah EM, El-Desoky E-SI, Etman HA, Youssef I, Soliman AMJ. Heterocycl Chem 2018; 55: 2959
• 2e Zhao Y, Duan Q, Zhou Y, Yao Q, Li Y. Org Biomol Chem 2016; 14: 2177
• 2f Xu H, Zhou B, Zhou P. et al. Chem Commun 2016; 52: 8002
• 2g Wan J-P, Cao S, Liu Y. Org Lett 2016; 18: 6034
• 3a Brandt CA, Silva ACMPD, Pancote CG, Brito CL, Silveira MABD. Synthesis 2004; 10: 1557
• 3b Thorwirth R, Stolle A. Synlett 2011; 15: 2200
• 4a Rafiee E, Joshaghani M, Eavani S, Rashidzadeh S. Green Chem 2008; 10: 982
• 4b Um I-H, Lee E-J, Seok J-A, Kim KH. J Org Chem 2005; 70: 7530
• 4c El-Taweel FMAA, Elnagdi MH. J Heterocycl Chem 2001; 38: 981
• 5 Kim J, Hong SH. Chem Sci 2017; 8: 2401
• 6 Wu W, Wang Z, Shen Q, Liu Q, Chen H. Org Biomol Chem 2019; 17: 6753
• 7 Reyno RS, Sugunan A, Ranganayakulu S, Suresh CH, Rajendar G. Org Lett 2020; 22: 1040
• 8a Kumar M, Vishwakarma RK, Preeti, Singh KN. New J Chem 2023; 47: 2412
• 8b Kumar M, Sharma AK, Ishu K, Singh KN. J Org Chem 2024; 89: 9888
• 8c Kumar M, Sharma AK, Ishu K, Singh KN. Org Lett 2024; 26: 10517
• 8d Preeti, Kumar M, Jaiswal A, Singh KN. Asian J Org Chem 2022; 11: e202100389
• 8e Vishwakarma RK, Kumar S, Singh KN. Org Lett 2021; 23: 4147
• 8f Chand S, Pandey AK, Singh R, Singh KN. J Org Chem 2021; 86: 6486
• 9 Sultana S, Shim J-J, Kim SH, Lee YR. Org Biomol Chem 2018; 16: 6749
• 10a Li J-S, Xie X-Y, Jiang S. et al. Org Chem Front 2021; 8: 697
• 10b Yao G, Wang B-F, Yang S, Zhang Z-X, Xu H-H, Tang R-Y. RSC Adv 2019; 9: 3403