771-17-5Relevant academic research and scientific papers
Superelectrophilic Activation of Crotonic/Methacrylic Acids: Direct Access to Thiochroman-4-ones from Benzenethiols by Microwave-Assisted One-Pot Alkylation/Cyclic Acylation
Vaghoo, Habiba,Prakash, G. K. Surya,Narayanan, Arjun,Choudhary, Rohit,Paknia, Farzaneh,Mathew, Thomas,Olah, George A.
supporting information, p. 6170 - 6173 (2016/01/09)
An efficient microwave-assisted protocol for the synthesis of 2-/3-methylthiochroman-4-ones by superacid-catalyzed alkylation followed by cyclic acylation (cyclization via intramolecular acylation) is described. Using easily accessible benzenethiols and crotonic acid/methacrylic acid with triflic acid (as catalyst of choice for needed optimal acidity), the reaction was tuned toward the formation of the cyclized products in good selectivity and yield. A mechanism involving the formation of carbenium-carboxonium superelectrophilic species is suggested.
Development of a chiral bis(guanidino)iminophosphorane as an uncharged organosuperbase for the enantioselective amination of ketones
Takeda, Tadahiro,Terada, Masahiro
supporting information, p. 15306 - 15309 (2013/11/06)
Chiral bis(guanidino)iminophosphoranes were designed and synthesized as chiral uncharged organosuperbase catalysts that facilitate activation of less-acidic pro-nucleophiles. The newly developed bis(guanidino) iminophosphoranes, which possess the highest basicity among chiral organocatalysts reported to date, were proven to be a superb class of chiral organosuperbases by reaction of azodicarboxylates with 2-alkyltetralones and their analogues as the less acidic pro-nucleophiles.
Thiacycloalkynes for copper-free click chemistry
De Almeida, Gabriela,Sletten, Ellen M.,Nakamura, Hitomi,Palaniappan, Krishnan K.,Bertozzi, Carolyn R.
supporting information; experimental part, p. 2443 - 2447 (2012/04/23)
The heteroatom helps! The introduction of an endocyclic sulfur atom enables fine-tuning of the reactivity and stability of thiacycloalkynes for copper-free click chemistry. The stabilizing effect of the endocyclic sulfur atom allows the use of highly activated seven-membered rings as reagents for bioorthogonal copper-free click chemistry. Copyright
ACYL RADICAL CYCLIZATIONS IN SYNTHESIS. PART 2. FURTHER SUBSTITUENT EFFECTS ON THE MODE AND EFFICIENCY OF CYCLIZATION OF 6-HEPTENOYL RADICALS.
Crich, David,Eustace, K. Angeline,Fortt, Simon M.,Ritchie, Timothy J.
, p. 2135 - 2148 (2007/10/02)
In an attempt to determine the factors affecting exo-/endo-selectivity in the cyclization of 6-heptenoyl radicals various heteroatom substituted selenol esters were prepared and reacted with tributyltin hydride.The incorporation of a 7-phenylthio moity re
CARBONYL RADICAL CYCLIZATIONS: PREPARATION OF SOME HETEROCYCLIC KETONES
Crich, David,Eustace, K. Angeline,Ritchie, Timothy J.
, p. 67 - 70 (2007/10/02)
It has been possible to synthesize 3-methylchromanone, 3-methylthiochromanone and 2,3-dihydro-3-methylquinolin-4-one from salicylic acid, thiosalicylic acid and anthranilic acid respectively by carbonyl radical cyclizations.
