Microwave-assisted synthesis of azetidines in aqueous media

Burkett, Brendan A.; Ting, Samuel Z.Y.; Gan, Gwendolyn C.S.; Chai, Christina L. L.

doi:10.1016/j.tetlet.2009.09.063

Cited by 20 publications

(11 citation statements)

References 29 publications

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“…[30,31] Six azetidinium-based ILs were synthesized by a two-step method including quarternization and metathesis reactions (Scheme 2). [32] Two isomers of 9 were synthesized by a similar procedure (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

Azetidinium‐based Hypergolic Ionic Liquids with High Strain Energy

Zheng

Zhang

et al. 2018

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A class of azetidinium-based hypergolic ionic liquids was synthesized and characterized by 1 H and 13 C NMR, IR spectroscopies, and electrospray ionization mass spectrometry. The properties of six synthesized ionic liquids were characterized with respect to liquid range (À80-200 8C), density (0.99-1.05 g cm À3 ), heat of formation (0.70-2.17 kJ g À1 ), specific impulse (164.0-184.5 s), and ignition delay time (23-130 ms). In order to better understand the relation between ring stains and energy of obtained compounds, the isomers of 9 were also synthesized for comparison. It is interesting to find that, compared with the isomers (9 a: 0.41 kJ g À1 , 156.5 s; 9 b: 0.36 kJ g À1 , 155.3 s), 9 exhibited a much higher heat of formation (0.78 kJ g À1 ) and specific impulse (164.8 s), which indicates that ring strains play an important role in the performance of energetic compounds. With the highest energetic properties (2.17 kJ g À1 , 184.5 s), 12 has a greater potential to be employed as green propellants.

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Section: Resultsmentioning

confidence: 99%

Azetidinium‐based Hypergolic Ionic Liquids with High Strain Energy

Zheng

Zhang

et al. 2018

ChemistrySelect

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“…(16.23)]. The results were excellent in terms of yields (65-92%), The importance of [1,4]oxazinones in biological systems has attracted great interest owing to their medicinal and pharmacological characteristics. A highly efficient synthesis of substituted benzo [1,4]oxazin-2-ones under microwave irradiation via a Smile rearrangement was reported by Shin and co-workers [138].…”

Section: Synthesis Of Benzothiazinones and Benzooxazinonesmentioning

confidence: 95%

“…Burkett et al reported an efficient methodology for accessing simple azetidines though cyclization of 3-(N-alkylamino)propyl sulfates furnished from the reaction of primary amines with the cyclic sulfate of 1,3-propanediol (Scheme 16.1). A feature of this cyclization included the accelerated synthesis (15 min) of azetidines in water under the influence of microwave-assisted heating [1].…”

Section: Synthesis Of Azetidinesmentioning

confidence: 99%

“…This regioselective approach is better than the methods reported in the literature in terms of robustness and orthogonality, and allowed the systematic construction of a small library of compounds in good yields (Scheme 16.10). A series of functionalized 3,6-disubstituted [1,2,4]triazolo [4,3-b]pyridazines were built from 3,6-dichloropyridazine and hindered N-acylhydrazines at 150 • C using catalytic conditions (5% AcOH) for M1 antagonist screening [101].…”

Section: Synthesis Of Tetrahydroindazolones and Pyridazine Derivativesmentioning

confidence: 99%

“…For heterocyles containing sulfur moieties, benzo[b] [1,4]thiazin-3(4H)-one derivative scaffolds are classified as privileged structures owing to the large number of biologically active molecules and natural products containing this moiety. A new method [137] using microwave irradiation provided these compounds via a Smile rearrangement from substituted 2-chlorobenzenethiols, chloroacetyl chloride, and primary amines [Eq.…”

Section: Synthesis Of Benzothiazinones and Benzooxazinonesmentioning

confidence: 99%

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