The activating effects of arylazo groups on a double bond. Preparation and properties of some bis(diaikylamino)arylazoethenes and related compounds

Gilchrist, T. L.; Stevens, John A.; Parton, Brian

doi:10.1039/p19850001737

Cited by 9 publications

(1 citation statement)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These results suggest a stepwise addition of the electron rich olefin to the dichloroazodiene. No reports of successful cyclization reactions with dichloroazodienes have appeared; however, several authors mention the preparation and addition elimination reactions of these compounds …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Reactions of Haloazodienes. A New and General Synthesis of Substituted Pyridazines

et al. 1996

View full text Add to dashboard Cite

The reaction of dihalohydrazones with Hünig's base gives 1-carbethoxy-3-phenyl-4-haloazodienes in-situ, which were found to combine with a variety of electron rich olefins to yield halo-substituted tetrahydropyridazines (Scheme 2 and Table 1 ). These haloazodiene cyclizations are best characterized as inverse electron demand, 4 + 2 hetero Diels-Alder reactions that maintain a high degree of regio- and stereochemical control (Schemes 5 and 6). The chloro-substituted tetrahydropyridazines that are formed give high yields of substituted pyridazines upon treatment with base (Table 1). The sequence of a chloroazodiene cyclization to a tetrahydropyridazine followed by an aromatization constitutes a new and general synthesis of substituted pyridazines. In contrast to the haloazodiene cyclizations, the novel cyclization reactions of the in-situ generated 1-carbethoxy-3-phenyl-4,4-dichloroazodiene were found to give N-aminopyrroles and pyridazines when combined with acyclic enamines (Table 3 ). However, reactions with cyclic enamines gave the N-aminopyrroles, pyridazines, a dihydropyridazine as products as well as the noncyclized enamine intermediates (Table 4 ). The noncyclized enamines could be converted to the N-aminopyrroles simply upon heating to higher temperatures, indicating a stepwise mechanism (Schemes 8 and 9). The examples described here are the first reported cyclization reactions for dichloroazodienes.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis and Reactions of Haloazodienes. A New and General Synthesis of Substituted Pyridazines

et al. 1996

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: THE ACTIVATING EFFECTS OF ARYLAZO GROUPS ON A DOUBLE BOND. PREPARATION AND PROPERTIES OF SOME BIS(DIALKYLAMINO)ARYLAZOETHENES AND RELATED COMPOUNDS

Gilchrist¹,

Stevens²,

Parton³

1985

Chemischer Informationsdienst

View full text Add to dashboard Cite

show abstract

Dichloro‐Substituted 1,2‐Diazabuta‐1,3‐dienes as Highly Reactive Electrophiles in the Reaction with Amines and Diamines: Efficient Synthesis of α‐Hydrazo Amidinium Salts

et al. 2018

View full text Add to dashboard Cite

The reaction of 4,4‐dichloro‐1,2‐diazabuta‐1,3‐dienes with various amines and diamines was studied. We found that in this reaction, the starting diazabutadienes behave as highly reactive electrophiles to open up a straightforward route to the corresponding amidinium salts with a hydrazone functionality in the adjacent position. The reaction was found to be very general; as a rule, all the products could be prepared in almost quantitative yields. We also demonstrated that the prepared amidinium salts could be used as versatile building blocks for the synthesis of polyfunctional molecules.

show abstract

The activating effects of arylazo groups on a double bond. Preparation and properties of some bis(diaikylamino)arylazoethenes and related compounds

Cited by 9 publications

References 2 publications

Synthesis and Reactions of Haloazodienes. A New and General Synthesis of Substituted Pyridazines

Synthesis and Reactions of Haloazodienes. A New and General Synthesis of Substituted Pyridazines

ChemInform Abstract: THE ACTIVATING EFFECTS OF ARYLAZO GROUPS ON A DOUBLE BOND. PREPARATION AND PROPERTIES OF SOME BIS(DIALKYLAMINO)ARYLAZOETHENES AND RELATED COMPOUNDS

Dichloro‐Substituted 1,2‐Diazabuta‐1,3‐dienes as Highly Reactive Electrophiles in the Reaction with Amines and Diamines: Efficient Synthesis of α‐Hydrazo Amidinium Salts

Contact Info

Product

Resources

About