AIBN-Promoted Synthesis of Bibenzo[b][1,4]thiazines by the Condensation of 2,2′-Dithiodianiline with Methyl Aryl Ketones

Abstract

A series of bibenzo[ b][1,4]thiazines with various functional groups has been synthesized by a free-radical condensation reaction. Bibenzo[ b][1,4]thiazines were obtained in moderate to good yield (up to 85%) through a one-step reaction of readily available 2,2'-dithiodianiline and methyl aryl ketones with AIBN as radical initiator in HOAc. Bibenzo[ b][1,4]thiazines exhibit diversiform solid-state packing.

Umpolung Strategy with 2‐Aminothiophenols: Access to 2‐Arylbenzothiazine Derivatives from Alkyl Aryl Ketones

“…Recently, 3 aa analogues were obtained via a reaction of 2,2′‐dithiodianilines and acetophenones in HOAc under aerobic conditions. One of the major disadvantages of this method is the use of AIBN [8] . This unstable initiator should be stored at low temperature in the dark to avoid thermal and photochemical decomposition and accidental explosion.…”

“…One of the major disadvantages of this method is the use of AIBN. [8] This unstable initiator should be stored at low temperature in the dark to avoid thermal and photochemical decomposition and accidental explosion. Moreover, the reactions were reported only with 2,2'-dithiodianilines, which should be prepared from their monomeric precursors 2-aminothiophenols by an additional oxidation.…”

The crystal structure of 13-ethoxycarbonyl-9-methyl-4-chlor-11-thioxo-8-oxa-10,12-diazatricyclo[7.3.1.02,7]trideca-2,4,6-triene, C14H15ClN2O3S

“…As we know, heterocyclic compounds containing N atoms exhibit important biological activities, pharmaceutical properties and the function of constructing metal complexes, etc. [3][4][5][6][7]. Among the N-heterocyclic compounds, 3,4-dihydropyrimidin-2-ones, 3,4-dihydropyrimidin-2-thiones compounds have been widely used in the field of antiviral [8], antitumor [9] and antibacterial activities [10].…”

Iodine‐Catalyzed Double [4+2] Oxidative Annulations for the Synthesis of Bipyrazines from Ketones and Diamines by a Domino Strategy

“…Very recently, there were a few reports demonstrated the access of dimeric benzothiazines by condensation of aryl methyl ketones with 2-aminothiophenols or disulfanediyldianilines. [13] However, to the best of our knowledge, no report on double oxidative annulations of ketones and diamines for the construction of dimeric pyrazine skeleton has been shown. The methods for the synthesis of dimeric pyrazines are primarily dependent on transition metal-catalyzed procedures, involving Suzuki, [14] Heck, [15] Stille, [16] Ullmann [17] and Negishi couplings, [18] as well as other coupling methods [19] (Scheme 1c).…”