52866-95-2Relevant academic research and scientific papers
NEW FACILE SYNTHESIS OF N-SULFINYLAMINE DERIVATIVES USING N,N'-SULFINYLBISIMIDAZOLE AND N-(CHLOROSULFINYL)IMIDAZOLE
Kim, Yong Hae,Shin, Jai Moo
, p. 3821 - 3824 (1985)
Treatment of amine derivatives such as amines, sulfonamides, and amides with N,N'-sulfinylbisimidazole (1) and N-(chlorosulfinyl)imidazole (2) in situ respectively gives the corresponding N-sulfinylamine derivatives (3): the latter reaction using N-(chlor
Synthesis, characterization, and cycloaddition reactivity of a monocyclic aromatic 1,2,3,5-tetrazine
Wu, Zhi-Chen,Boger, Dale L.
supporting information, p. 16388 - 16397 (2019/10/16)
Herein we disclose the synthesis and full characterization of the first monocyclic aromatic 1,2,3,5-tetrazine, 4,6-diphenyl-1,2,3,5-tetrazine. Initial studies of its cycloaddition reactivity, mode, regioselectivity, and scope illustrate that it participates as the 4π-component of well-behaved inverse electron demand Diels-Alder reactions where it preferentially reacts with electron-rich or strained dienophiles. It was found to exhibit an intrinsic reactivity comparable to that of the isomeric 3,6-diphenyl-1,2,4,5-tetrazine, display a single mode of cycloaddition with reaction only across C4/N1 (no N2/N5 cycloaddition observed), proceed with a predictable regioselectivity (dienophile most electron-rich atom attaches to C4), and manifest additional reactivity complementary to the isomeric 1,2,4,5-tetrazines. It not only exhibits a remarkable cycloaddition reactivity, surprisingly good stability (e.g., stable to chromatography, long-term storage, presence of H2O even as reaction co-solvent), and broad cycloaddition scope, but it also displays powerful orthogonal reactivity with the 1,2,4,5-tetrazines. Whereas the latter reacts at extraordinary cycloaddition rates with strained dienophiles (tetrazine ligation), the new and isomeric 1,2,3,5-tetrazine displays similarly remarkable cycloaddition rates and efficiencies with amidines (1,2,3,5-tetrazine/amidine ligation). The crossover reactivities (1,2,4,5-tetrazines with amidines and 1,2,3,5-tetrazines with strained dienophiles) are sufficiently low to indicate they may be capable of use concurrently without competitive reactions.
Reaction of electron-deficient N-sulfinylanilines with chiral α-hydroxy acids: A new process for the synthesis of enantiomerically pure α-hydroxy amides
Chidambaram,Zhu,Penmetsa,Kronenthal,Kant
, p. 6017 - 6020 (2007/10/03)
A practical procedure to prepare enantiomerically pure α-hydroxy amides from chiral α-hydroxy acids and electron-deficient anilines via N-sulfinylaniline derivatives has been developed. (C) 2000 Elsevier Science Ltd.
6?-Cycloadditions of Aryl and New Heteroaryl N-Sulphinylamines With 2,3-Dimethylbuta-1,3-diene: Synthesis, Kinetics, Substituent Effects, Theoretical Calculations, and Reaction Mechanism
Butler, Richard N.,O'Halloran, Gerard A.,Burke, Luke A.
, p. 1855 - 1860 (2007/10/02)
A range of new N-sulphinylamine derivatives of heteroaryl rings, including tetrazoles, oxadiazoles, thiadiazoles, thiazoles, and oxazoles is reported.The influence of the -N=S+-O- group on the n.m.r. spectra of the ring to which it i
1,2-Thiazines and Related Heterocycles. Part 1. An Investigation of the Cycloadditions of N-Sulphinylanilines with 1,4-Epoxy-1,4-dihydronaphthalene and Other Alkenes
Hanson, Peter,Lewis, Robin J.,Stone, Thomas W.
, p. 1719 - 1724 (2007/10/02)
Evidence is adduced from the character of the alkenes which cycloadd to N-sulphinylanilines and from a kinetic investigation of the reactions of N-sulphinylanilines with 1,4-epoxy-1,4-dihydronaphthalene, examining the effects upon reaction rate of solvent polarity, temperature, and substitution in the N-sulphinylanilines, that the cycloadditions are pericyclic reactions of Diels-Alder type with inverse electron demand.A degree of charge separation in the transition state is indicated but this is small and confined essentially to the sulphinylaniline moiety.
Heterocyclic Synthesis with Malonyl Dichloride. Part 13. 6-Chloro-4-hydroxy-2-oxypyran-3-carboxanilides from N-Sulphinylanilines and Further Reactions of Malonyl Dichloride with Thiocyanates
Al-Ajely, Mohammed S.,Al-Rawi, Jasim M. A.,Elvidge, John A.
, p. 1575 - 1578 (2007/10/02)
N-Sulphinylanilines react with malonyl dichloride to give 6-chloro-4-hydroxy-2-oxopyran-3-carboxanilides with loss of the sulphoxide moiety as thionyl chloride.Milder conditions and electron-withdrawing substituents do not alter the course of the reaction of thiocyanates with malonyl dichloride to give 2-substituted-thio-7-chloro-4H,5H-pyranooxazine-4,5-diones.
