Synthesis of 2,3-bifunctional imidazo[1,2-a]pyridines through cycloadditions of pyridinium ylides with N-cyano-4-methyl-N-phenylbenzenesulfonamide

Zhan, Gu; Zhao, Hongli; Li, Dong-Ai; Wu, Yuling; Fang, Huaying; Peng, Cheng; Han, Bo

doi:10.1016/j.tetlet.2022.154295

Search citation statements

Order By: Relevance

Paper Sections

Select...

Introduction1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article1

Relationship

Self Cite0

Independent1

Authors

Journals

Cited by 1 publication

(1 citation statement)

References 54 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Moreover, they are available, inexpensive, nontoxic, and at the same time resistant to air and moisture. In the last few decades, the use of quaternary pyridinium derivatives as versatile intermediates in organic synthesis has gained prominence [6a–g] . In particular, the Katritsky salts, typical quaternary pyridinium derivatives, are finding increasing use as intermediates for building C−C bonds [7a–c] …”

Section: Introductionmentioning

confidence: 99%

Diene Salts of the Adamantane Series: Synthesis, Structure, and Chemical Transformations

Bogdanova,

Baimuratov,

Polyakova

et al. 2024

Asian J Org Chem

View full text Add to dashboard Cite

Mono‐ and bis‐pyridinium, phosphonium and sulfonium allylic salts, containing adamantane fragment, have been obtained from the substitution reaction in 1,4‐dibromo‐2‐butene. It was found, that the attack of triethylamine undergoes from the sterically less hindered side, leading to deprotonation and subsequent elimination of the molecular fragment with the formation of a new salt of diene structure. Quantum chemical calculations were used to confirm the structure of one of the products by correlation analysis of experimental and calculated NMR data that confirmed the s‐cisoid conformation of the diene. It was found, that obtained dienes may be used as substrates in Diels‐Alder reaction despite their high sterical hinderance.

show abstract

Section: Introductionmentioning

confidence: 99%