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Additional resources for Advanced Problems in Organic Reaction Mechanisms
Me coc Me ocMe2 , N N / \ O 1 2 48. 2H 3 Propargylbenzotriazoles to Five-membered Heterocycles 1-Propargylbenzotriazole, readily available by alkylation of benzotriazole with propargyl bromide in the presence of sodium hydroxide, has been found to be a valuable building block for the synthesis of furans, dihydrofurans, pyrroles and indoles. The versatility of this type of chemistry for the synthesis of otherwise difficultly accessible heterocyclic systems is illustrated by the following typical transformations.
I 1 o 2 50. 3 Isoxazoles from Cyclopropanes Treatment of 2-aryl-l,l-dichlorocyclopropanes 1 under nitrating conditions with mixed acid at 0~ can give 3-aryl-5-chloroisoxazoles in yields of up to 85% depending on the nature of substituents in the aryl ring. The transformation is most efficient when the aromatic substituent is electron withdrawing (R = 4-NO2, 85%; R = 3-NO2, 31%; R = 2-NO2, 13%), but is very poor with electron donating groups (R = 4-Me, 2%; R = 4-MeO, only degradation products). Suggest a mechanism for isoxazole formation which accounts for these observations.
Give a mechanistic explanation for this transformation. O O ~ Me O R R R R 1 R = H, alkyl, vinyl 2 83. m-Terphenyls from Pyrones Alkali-catalysed reaction of the pyrones 1 with acetophenones ArlCOMe in DMF at room temperature results in smooth transformation into the m-terphenyls 2 (50-66%) and the pyranylideneacetates 3 (0-28%). Give mechanisms to account for the formation of 2 and 3 from 1. SMe SMe O2Me Ar Ar Ar~ ]~ CO -12Me Al Ar1 1 2 84. CO2Me 3 A Cascade Reaction Treatment of the readily accessible ester 1 with either Ac20/TsOH/refluxing xylene or TFAA/Et3N/CH2C12/RT or TMSOTf/Et3N/CH2C12/RT results in smooth conversion into the indoline 2 in 50-75% yield depending on the conditions employed.
Advanced Problems in Organic Reaction Mechanisms by McKillop