TY - JOUR
T1 - Practical synthesis and biological screening of sulfonyl hydrazides
AU - Macara, João
AU - Caldeira, Catarina
AU - Cunha, José
AU - Coelho, Jaime A. S.
AU - Silva, Maria J. S. A.
AU - Krämer, Konrad
AU - Grathwol, Christoph W.
AU - Bräse, Stefan
AU - Marques, M. Manuel B.
N1 - Funding Information:
info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50006%2F2020/PT#
info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50006%2F2020/PT#
info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04378%2F2020/PT#
We thank the FCT for fellowships: SFRH/BD/142864/2018 (J. M.), Scientific Employment Stimulus 2020/02383/CEECIND (J. A. S. C.).
The National NMR facility is supported by the FCT (ROTEIRO/0031/2013 –PINFRA/22161/2016, co-financed by FEDER through COMPETE 2020, POCI, and PORL and FCT through PIDDAC).
Publisher Copyright:
© 2023 The Royal Society of Chemistry.
PY - 2022/12/21
Y1 - 2022/12/21
N2 - A methodology for the synthesis of sulfonyl hydrazides mediated by hypervalent iodine is described. Taking advantage of the umpolung properties of hypervalent iodine reagents, the polarity of sodium sulfinate salts is reversed, and a key intermediate is generated and reacted with mono- and disubstituted hydrazines. To highlight the practical utility of this protocol, a diverse range of sulfonyl hydrazides were synthesized in yields up to 62%. Furthermore, a gram-scale reaction was performed, showing the robustness of the procedure. Mechanistic studies, including DFT calculations, were performed and the bioactivity of the generated compounds was evaluated.
AB - A methodology for the synthesis of sulfonyl hydrazides mediated by hypervalent iodine is described. Taking advantage of the umpolung properties of hypervalent iodine reagents, the polarity of sodium sulfinate salts is reversed, and a key intermediate is generated and reacted with mono- and disubstituted hydrazines. To highlight the practical utility of this protocol, a diverse range of sulfonyl hydrazides were synthesized in yields up to 62%. Furthermore, a gram-scale reaction was performed, showing the robustness of the procedure. Mechanistic studies, including DFT calculations, were performed and the bioactivity of the generated compounds was evaluated.
UR - http://www.scopus.com/inward/record.url?scp=85146260576&partnerID=8YFLogxK
U2 - 10.1039/d2ob02160a
DO - 10.1039/d2ob02160a
M3 - Article
C2 - 36606485
AN - SCOPUS:85146260576
SN - 1477-0520
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
ER -