Citation: Chen Yan, Jing Sun, Chao-Guo Yan. Convenient construction of spiro[indoline-3, 5'-pyrrolo[3, 4-c]carbazole] and spiro[indene-2, 5'-pyrrolo[3, 4-c]carbazole] via acid-catalyzed Diels-Alder reaction[J]. Chinese Chemical Letters, ;2021, 32(3): 1253-1256. doi: 10.1016/j.cclet.2020.08.052 shu

Convenient construction of spiro[indoline-3, 5'-pyrrolo[3, 4-c]carbazole] and spiro[indene-2, 5'-pyrrolo[3, 4-c]carbazole] via acid-catalyzed Diels-Alder reaction

College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, China

cgyan@yzu.edu.cn

Received Date: 21 July 2020
Revised Date: 21 August 2020
Accepted Date: 31 August 2020
Available Online: 2 September 2020

Figures(7)

p-TsOH catalyzed Diels-Alder reaction of 3-(indol-3-yl)maleimides with 3-phenacylideneoxindoles in toluene at 80 ℃ for two hours afforded cis/trans isomers of 3a', 4′, 6′, 10c'-tetrahydrospiro[indoline-3, 5′-pyrrolo[3, 4-c]carbazoles] in nearly comparable yields, which could be easily converted to the corresponding 4′, 6′-dihydrospiro[indoline-3, 5′-pyrrolo[3, 4-c]carbazole] in high yields and with high diastereoselectivity by further DDQ oxidation., the similar reaction of 3-(indol-3-yl)maAdditionallyleimides with 2-arylidene-1, 3-indanediones in toluene 80 ℃ and sequential DDQ oxidation afforded functionalized dihydrospiro[indene-2, 5′-pyrrolo[3, 4-c]carbazoles] as major products.
- Carbazole,
- Spiroixindole,
- Maleimides,
- 1, 3-Indanedione,
- Diels-Alder reaction
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