Addition and cycloaddition reactions of β-chloroazo-olefins

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

doi:10.1039/p19850001741

Cited by 27 publications

(13 citation statements)

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“…This study is devoted to a detailed investigation of this reaction to give the corresponding amidinium salts. Moreover, our results reveal that the structure of the products is different from the structure published in the literature (Scheme ).…”

Section: Introductioncontrasting

confidence: 89%

“…For example, the antimicrobial drug Pentamidine contains this functional group. [7] Compound 2a crystallizes in the monoclinic space group C2/c, and represents a salt consisting of the 4λ 4 -morpholinium cation and a chloride anion (Scheme 1). The (Z,E)-4,4′-[2-(2phenyl-hydrazono)ethane-1,1-diylidene] fragment of the cation is planar (rms deviation is 0.011 Å).…”

Section: Resultsmentioning

confidence: 99%

“…It should be noted that 5,6-dihydro-1H-imidazo[1,2-e][1,2,3]triazoles 8 represent a rare type of heterocyclic structure. As far as we know, only one example of a similar compound (a derivative of 1H-benzo [4,5]imidazo[1,2-c][1,2,3]triazole) has been reported in the literature. [8] Compound 8c is a bicycle that includes 1,2,3-triazole and 5,6-dihydro-1H-imidazole rings: Finally, we found that other primary and secondary aliphatic amines can participate in this reaction to give the corresponding amidinium salts 9a-14a.…”

Section: Resultsmentioning

confidence: 99%

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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

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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.

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Section: Introductioncontrasting

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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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

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“….432( 3 ) .350(3) .4 1 3( 3) .484 (4) .324(3) .479( 3) .386(3) .38 I(4) .382 (4) .362( 5) .371( 5 --The azoalkene 2 has been used by Sommer with dimethyl azodicarboxylate (see above),22 and with Nsulphinyl compounds 2 1 in cycloadditions. It was prepared in a reported yield of 44"/d [m.p.…”

Section: Diversity Of Reaction Of Azoalkenes In Cycloadditionsmentioning

confidence: 99%

Diversity of reaction of azoalkenes in cycloadditions

Ferguson¹,

Lough²,

Mackay³

et al. 1991

J. Chem. Soc., Perkin Trans. 1

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“…The structure of the obtained compounds (particularly, mutual disposition of Me and Ph substituents) was established by NOE 2D NMR (Scheme 34, the position of substituents in the starting quinolinone is indicated). 118 The 108,114 It should be noted that cycloadducts 86 were obtained only for N-substituted indoles but in low yields. 114 Chiral diazabutadienes 74 containing the D-arabinose residue do not react with diethyl acetylenedicarboxylate.…”

Section: Scheme 31mentioning

confidence: 99%