Zhou, Quan; Snider, Barry B. published their research in Journal of Organic Chemistry on December 3 ,2010. The article was titled 《Synthesis of Hexacyclic Parnafungin A and C Models》.Category: bromides-buliding-blocks The article contains the following contents:
Unstable hexacyclic parnafungin A and C models isoxazolophenanthridones I (R = R1 = H; R = MeO, R1 = H; R = H, R1 = MeO) and benzopyranoisoxazolophenanthridinediones II (R2 = H, Me) were prepared using Suzuki coupling reactions, reductive cyclizations of o-nitrobenzoates to benzisoxazolones and the cyclocondensations of hydroxymethylarylbenzisoxazolones to fused isoxazoloquinolines as key steps. Iodoxanthones III (R2 = H, Me) were prepared in four or five steps and 33-50% overall yields from Me salicylate and either 5-Me or 5-(hydroxymethyl)resorcinol; Suzuki-Miyaura coupling of III (R2 = H, Me) with an excess of readily available 3-carbomethoxy-2-nitrophenyl pinacolboronate (prepared in three steps from 3-methyl-2-nitro-1-bromobenzene) afforded the hindered highly functionalized (methoxycarbonyl)nitrophenyl-substituted xanthones in 53-58% yields. Zinc reduction of the (methoxycarbonyl)nitrophenyl-substituted xanthones gave benzisoxazolinones that were treated with MsCl and then with base to generate the unstable hexacyclic parnafungin A and C models II (R = H) and II (R = Me) in 13% overall yield for 8 steps and in 8% overall yield for 9 steps, resp. Analogously to the parnafungins, II (R2 = Me) decomposes to a phenanthridine with a half-life of 2 d in CDCl3. The experimental part of the paper was very detailed, including the reaction process of 3-Bromo-2-nitrobenzoic acid(cas: 116529-61-4Category: bromides-buliding-blocks)
3-Bromo-2-nitrobenzoic acid(cas: 116529-61-4) belongs to organobromine compounds.Depending on the type of carbon to which the bromine is bonded, organic bromide could be alkyl, alkenyl, alkynyl, or aryl. Due to the reactivity of bromide, they are used as potential precursors or important intermediates in organic synthesis. Category: bromides-buliding-blocks
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary