Chou, Teh-Chang; Cheng, Ju-Fang; Gholap, Atul R.; Huang, Jim Jing-Kai; Chen, Jyun-Chang; Huang, Jing-Kai; Tseng, Jui-Chang published the artcile< Aromatization-driven Grob-fragmentation approach toward polyazaacenes. Synthesis and amination of multi-functionalized diazapentacenes>, Synthetic Route of 27841-33-4, the main research area is dichloro dimethoxy tetrahydro methanoanthracene preparation Grob fragmentation; methoxycarbonyl chloro diazapentacene regioselective preparation amine amination; amino methoxycarbonyl diazapentacene preparation.
A general approach toward the synthesis of multi-functionalized diazapentacene derivatives I [R1 = R4 = H, nitro; R2 = R3 = H, MeO, nitro; R2R3 = 15-crown-5-ether, 18-crown-6-ether] using 1,2,3,4-tetrachloro-5,5-dimethoxycyclopentadiene (TDCp), a substituted benzene-1,2-diamine (ADA), and a naphthalene-1,4-dione (BQ) as the building units, was described. The synthesis basically entails three operations: (i) oxidation of the dichloroetheno-bridge in the Diels-Alder cycloadduct of TDCp and 1,4-naphthaquinone, (ii) condensation of the 1,2-diketone thus generated with an ADA to give quinoxaline-fused polycyclic compounds, followed by (iii) an one-pot, three-reaction process keyed upon the base- or acid-catalyzed aromatization-driven Grob-type fragmentation to produce compounds I. The compound I [R1 = R2 = R3 = R4 = H] underwent the nucleophilic aromatic ipso-amination with primary and secondary amines to afford the amino-substituted derivatives II [R5 = n-Bu, cyclohexyl, Ph, etc.], which tend to self-assemble in solid state driven by the cofacial π-stacking interactions, demonstrated by the crystal packing structures of compounds II [R5 = n-Bu, N1-(anthracen-9-ylmethyl)propane-1,3-diamino].
Tetrahedron published new progress about Amination. 27841-33-4 belongs to class chlorides-buliding-blocks, and the molecular formula is C8H12N2O2, Synthetic Route of 27841-33-4.
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics