Synthetic application of intramolecular anionic Diels-Alder reaction

2016 Fiscal Year Final Research Report

• Project/Area Number: 26410120
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Okayama University
• Principal Investigator: Kudoh Takayuki 岡山大学, 自然科学研究科, 助教 (00346412)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Keywords: カルバゾール / 分子内Diels-Alder反応 / アニオン / 1,6-ジイン / インドール

Outline of Final Research Achievements

We found that intramolecular dehydro Diels-Alder reaction of 1-indolyl-1,6-diynes proceeded smoothly under mild heating conditions and gave substituted carbazoles in moderate to good yields. The cycloaddition of 1-indolyl-1,6-diynes with conjugated substituents on alkyne termini showed high reactivity. We also found that the intramolecular cycloaddition of 1-indolyl-1,6-diynes bearing aryl substituent chemoselectively gave aryl-substituted carbazoles in high yields.

Free Research Field

有機合成化学