Reaction of 3-aroylaziridines with aryl isothiocyanates

Lown, J. W.; Dallas, G.; Maloney, T. W.

doi:10.1139/v69-589

Cited by 36 publications

(19 citation statements)

References 7 publications

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“…The 2-(2'-thieny1)aziridines bearing an Ncyclohexyl substituent reacted with a series of aryl isothiocyanates to give, after chromatography on alumina, 2-(2'-thieny1)-4-thiazolines and 2-arylimino-4-(2'-thieny1)-4-thiazolines ex- The previously postulated initial product of reactions compounds of type A were by far the 1,3-dipolar cycloaddition (10) of this tautomerization could be followed by n.m.r. (see Fig.…”

Section: (A) Acetylenic Dipolarophilesmentioning

confidence: 99%

1,3-Dipolar cycloaddition reactions of 2-(2′-thienyl)aziridines

Lown¹,

Matsumoto²

1970

Can. J. Chem.

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The 1,3-dipolar cycloaddition of 2-(2'-thieny1)aziridines to a series of acetylenic and heterornultiple dipolarophiles leading to a series of new linked heterocycles is described. The versatility of these reactions suggests a general synthetic route to linked heterocycles.Canadian Journal of Chemistry, 48, 3399 (1970) We have recently described the preparation of the hitherto unknown 2-(2'-thieny1)aziridines (1) and have shown that, despite the lower resonance energy of the thiophene ring (20 kcal mole-' (2)) compared with benzene, 2-(2'-thieny1)-3-aroylaziridines undergo thermal cleavage of the 2-3 bond of the aziridine ring to azomethine u ylides at moderate temperatures. The transient dipoles could be trapped with olefinic dipolarophiles affording 2-(2'-thieny1)pyrrolidines.We report the examination of 1,3-dipolar cycloadditions of 2-(2'-thieny1)aziridines to acetylenic and heteromultiple bonds as a first approach to a general synthesis of linked heterocycles. (a) Acetylenic DipolarophilesBoth cis-and trans-3-benzoyl-l-cyclohexyl-2-(2'-thieny1)aziridine (1) reacted with dimethyl ~6~1 1 3 yl-3-deutero-2-(2'-thieny1)aziridine (91 % deuterium incorporation) gave 5 in which both branches of the 12 Hz AB quartet due to the methine protons were diminished to an equal extent (20 %). This discounts the trans-3-pyrroline structure 4 for the compound (which is in any case unlikely in view of the magnitude of the methine coupling) which would be expected to show one branch of the AB quartet diminished I C6Hll

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Section: (A) Acetylenic Dipolarophilesmentioning

confidence: 99%

1,3-Dipolar cycloaddition reactions of 2-(2′-thienyl)aziridines

Lown¹,

Matsumoto²

1970

Can. J. Chem.

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“…The most frequent type of 1,3-dipolar cycloaddition reaction of azomethine ylides is that with alkenyl or alkynyl dipolarophiles substituted with electron-withdrawing groups, providing access to pyrrolidine-containing molecules of biological [18,[22][23][24][25][26] or materials science interest [27][28][29][30][31]. The reactions with multiple bonded heteroatom systems such as carbonyl, thiocarbonyl, isothiocyanato, imino, isocyanato, nitrile, nitroso, and azo derivatives are also known, but less well studied [7,16,[32][33][34][35][36][37][38]. Less recognized is the ability of azomethine ylides to react with aromatic dipolarophiles when the aromatic system is embedded within a polycyclic aromatic hydrocarbon, tethered with the azomethine ylide (an intramolecular process) or substituted with highly electron withdrawing nitro groups [39].…”

Section: Introductionmentioning

confidence: 99%

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives

Meyer

Ryan

2016

Molecules

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Abstract:We provide a comprehensive account of the 1,3-dipolar cycloaddition reactions of azomethine ylides with carbonyl dipolarophiles. Many different azomethine ylides have been studied, including stabilized and non-stabilized ylides. Of the carbonyl dipolarophiles, aldehydes including formaldehyde are the most studied, although there are now examples of cycloadditions with ketones, ketenes and carboxyl systems, in particular isatoic anhydrides and phthalic anhydrides. Intramolecular cycloadditions with esters can also occur under certain circumstances. The oxazolidine cycloadducts undergo a range of reactions triggered by the ring-opening of the oxazolidine ring system.

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“…The reaction is analogous to the deacylation involved in the last step of the Knorr pyrrole synthesis (24) (eq. [5]), and also the observed dehydrogenative elimination of an aroyl group from a 2-iminothiazolidine by the action of quinones in acetic acid (25) For personal use only.…”

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confidence: 96%

Thermal [2 + 3] cycloaddition of N-trichloroacetyldiphenylcyclopropenimine to 3-aroylaziridines and 3-carbomethoxyaziridines

Lown¹,

Westwood²,

Moser³

1970

Can. J. Chem.

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N-Trichloroacetyldiphenylcyclopropenimine reacted with either cis-or trarzs-3-benzoyl-1-cyclohexyl-2-m-nitrophenylaziridine in a [2+ 31 cycloaddition to the C=N bond of the imine to form (a) 5-benzoyl-2-m-nitrophenyl-4-(spirodiphenylcyclopropene)-3-(trichloroacetylhydrate)-imidazolidine and (b) l-cyclohexyl-4-(cis-1,2-diphenylvinyl)-3-dichloroacetyl-2-n-nitrophenylimidazoline. Similar reactions with other 3-aroylaziridines gave analogous irnidazolidines and imidazolines. Isolation of an unhydrated imidazolidine of type (a) in the corresponding addition with 3-carbomethoxy-1-cyclohexyl-2-phenylaziridine gave direct spectroscopic proof for the cyclopropene moiety in these adducts. The orientation of the 1,3 dipolar additions was confirmed by a reaction using a specifically 3-deuterated aziridine.The isolation of these adducts of type (a) strongly supports the previously suggested intermediacy of an oxazolidine in the analogous addition of 3-aroylaziridines to diphenylcyclopropenone.

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Reaction of 3-aroylaziridines with aryl isothiocyanates

Cited by 36 publications

References 7 publications

1,3-Dipolar cycloaddition reactions of 2-(2′-thienyl)aziridines

1,3-Dipolar cycloaddition reactions of 2-(2′-thienyl)aziridines

1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides with Carbonyl Dipolarophiles Yielding Oxazolidine Derivatives

Thermal [2 + 3] cycloaddition of N-trichloroacetyldiphenylcyclopropenimine to 3-aroylaziridines and 3-carbomethoxyaziridines

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