2018
DOI: 10.1038/s41467-018-03085-3
|View full text |Cite
|
Sign up to set email alerts
|

Expedient syntheses of N-heterocycles via intermolecular amphoteric diamination of allenes

Abstract: Saturated 1,4-diazo heterocycles including piperazines, 1,4-diazepanes, and 1,4-diazocanes, are highly important for therapeutic development, but their syntheses are often tedious. We describe here an amphoteric diamination strategy to unite readily available 1,2-, 1,3- or 1,4-diamine derivatives with electron-deficient allenes via a formal [n + 2] (n = 4, 5, 6) cyclization mode to produce the corresponding 1,4-diazo heterocycles in just one step. This strategy features mild reaction conditions, high functiona… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
2

Citation Types

0
34
0

Year Published

2018
2018
2022
2022

Publication Types

Select...
7
1

Relationship

0
8

Authors

Journals

citations
Cited by 48 publications
(34 citation statements)
references
References 53 publications
0
34
0
Order By: Relevance
“…Because of this, saturated heterocycles have become increasingly crucial scaffolds for the development of new pharmaceutical compounds. However, unlike heteroaromatics, which can be synthesized conveniently via a variety of cross-coupling reactions, functionalized saturated heterocyclic ring systems have remained challenging to produce 5 7 . For example, the generation of 1,4-dioxane derivatives, which are prevalent in natural products and bioactive compounds (Fig.…”
Section: Introductionmentioning
confidence: 99%
“…Because of this, saturated heterocycles have become increasingly crucial scaffolds for the development of new pharmaceutical compounds. However, unlike heteroaromatics, which can be synthesized conveniently via a variety of cross-coupling reactions, functionalized saturated heterocyclic ring systems have remained challenging to produce 5 7 . For example, the generation of 1,4-dioxane derivatives, which are prevalent in natural products and bioactive compounds (Fig.…”
Section: Introductionmentioning
confidence: 99%
“…In this work, by employing ambiphilic coupling partners we successfully achieve the (hetero)annulation of AQ-directed nonconjugated alkenes 48 , thereby providing direct access to useful 2,3-dihydrobenzofurans, indolines, and indanes [49][50][51][52] . Mechanistic experiments and DFT studies shed light on the origins of diastereoinduction, anti-selectivity, and other aspects of this Pd(II)/ Pd(IV) annulation process.…”
mentioning
confidence: 99%
“…The residue was purified by column chromatography. 4,6,7,8,8ahexahydropyrrolo[1,pyrazine-8a-carboxamide (6a).White solid (Hexane/AcOEt, 2:1). Yield: 312 mg, 92 %.…”
Section: Discussionmentioning
confidence: 99%
“…M. p. 158-160 ºC. 1 H NMR (300 MHz, CDCl 3 ) δ: 7.70-7.66 (m, 2H), 7.37-7.30 (m, 3H), 6.00 (d,J = 8.3 Hz,1H),4H),1H) 6-oxo-1-phenyl-3,4,6,7,8,8ahexahydropyrrolo[1,2-a] -6-oxo-3,4,6,7,8,8ahexahydropyrrolo[1,2-a] 3,4,4,6,7,8,pyrazine-8acarboxamide (6d). Orange solid (Hexane/AcOEt, 3:1).…”
Section: Discussionmentioning
confidence: 99%
See 1 more Smart Citation