159682-53-8Relevant academic research and scientific papers
Cycloaddition chemistry of anhydro-4-hydroxy-1,3-thiazolium hydroxides (thioisomunchnones) for the synthesis of heterocycles
Padwa,Harring,Hertzog,Nadler
, p. 993 - 1004 (1994)
A series of α,α-disubstituted thioisomunchnones were prepared by treating acyclic or cyclic thioamides with bromoacetyl chloride in the presence of triethylamine. The resulting mesoionic dipole was found to undergo bimolecular 1,3-dipolar cycloaddition wi
On the intramolecular 1,4-dipolar cycloaddition reaction of thiazinium betaines for the construction of aza-, diaza-, and polyaza-heterocyclic ring systems
Padwa,Coats,Harring,Hadjiarapoglou,Semones
, p. 973 - 984 (2007/10/02)
A series of bicyclic anhydro-4-hydroxy-2-oxo-1,3-thiazinium hydroxides containing tethered π-systems are easily prepared from the reaction of thiolactams with 1,3-bielectrophiles. These cross-conjugated heteroaromatic betaines undergo regio- and stereospecific 1,4-dipolar cycloaddition in good yield to produce cycloadducts containing a carbonyl sulfide bridge which can be induced to lose COS on further heating. Two of the cycloadducts were characterized by single crystal X-ray determinations. Control of ring size in the final product of the cycloaddition can be achieved by variation of the dipolarophilic chain length. Entry to the [6,6,5]- and [6,6,6]pyridone ring systems was possible using phenylalkynyl-substituted thioamides. Intramolecular 1,4-dipolar cycloaddition of a thiazinium betaine dipole also occurs across an indolyl π-bond. With only one substituent group in the 9-position of the bicylic betaine, the reaction takes an entirely different course unless a highly activated π-bond is incorporated into the tether. The preferred reaction with modestly activated π-systems corresponds to loss of the activated proton to produce an S,N-ketene acetal. When a ketene S,S-acetal group was incorporated onto the side chain, the 1,4-dipolar cycloaddition reaction was facilitated relative to proton loss.
