24098-82-6Relevant academic research and scientific papers
Substrate scope in the direct imine acylation of ortho-substituted benzoic acid derivatives: The total synthesis (±)-cavidine Dedicated to the memory of Sandy McKillop - Colleague, mentor, collaborator and friend
Kitsiou, Christiana,Unsworth, William P.,Coulthard, Graeme,Taylor, Richard J.K.
, p. 7172 - 7180 (2015/06/23)
The direct imine acylation (DIA) and subsequent cyclisation of a range of imines with ortho-substituted benzoic acid derivatives is described. Variation in the coupling reagents, imine and benzoic acid were all examined. The DIA procedure was also applied in the total synthesis of (±)-cavidine.
Direct imine acylation: Rapid access to diverse heterocyclic scaffolds
Unsworth, William P.,Kitsiou, Christiana,Taylor, Richard J. K.
supporting information, p. 258 - 261 (2013/03/13)
A simple and efficient procedure to prepare a range of diverse heterocycles by the direct acylation of imines using a variety of functionalized benzoic acids is described. The methodology features a novel method for N-acyliminium ion generation followed by in situ intramolecular trapping by oxygen-, nitrogen-, sulfur-and carbon-based nucleophiles. Preliminary mechanistic studies, using ReactIR, are also reported.
REACTIONS OF o-(N-METHYLCARBAMOYL)PHENYL SULPHOXIDES WITH ELECTROPHILES
Uchida, Yuzuru,Oae, Shigeru
, p. 649 - 654 (2007/10/02)
Reactions of alkyl o-(N-methylcarbamoyl)phenyl sulphoxides 1 with various electrophiles, such as acetic anhydride, acetyl chloride, thionyl chloride and p-toluenesulphonyl chloride, have been carried out.Treatment of 1 with excess acetic anhydride in general leads to the formation of the Pummerer type rearrangement products or related products.In the reactions of 1 with acetyl, thionyl and p-toluenesulphonyl chlorides, 2-methyl-1,2-benzisothiazole-3(2H)-one, 4b, and alkyl chlorides were obtained nearly quantitatively.All these reactions can be rationalized on the basis of the initial O-acylation and subsequent either α-proton removal to result in the Pummerer rearrangement or nucleophilic attack of neighbouring carbamoyl group to afford the five-membered products 4b.
A novel cyclization reaction of o-carboxyphenyl and o-carbamoylphenyl sulfoxides. Formation of benzoxathiane, dihydrobenzothiazine and benzoisothiazoline derivatives
Oae,Numata
, p. 2641 - 2646 (2007/10/08)
When o-carboxyphenyl or o-carbamoylphenyl sulfoxide was heated with a large excess of acetic anhydride at 100-130° for 1-3 h, 6-membered heterocyclic compounds, i.e., 3,1 - benzoxathian-4 - one and 2,3 - dihydro - 1,3 - benzothiazin - 4 - one, and a 5-membered heterocyclic compound, i.e., 1,2-benzoisothiazolin-3-one were obtained in good yield. Cyclization would take place by the initial intramolecular nucleophilic attack of either the sulfinyl O atom at ortho-carbonyl carbon or the N atom of the amide group at ortho-sulfinyl S atom to give a 5-membered cyclic acyloxysulfonium salt or aminosulfonium salt, which undergoes an intramolecular Pummerer rearrangement to afford the heterocyclic compounds.
