o-Quinones Derived from Tribenzotriquinacenes: Functionalization of Inner Bay Positions and Use for Single-Wing Extensions

Zhang Y-F, Tian W-F, Cao X-P, Kuck D, Chow H-F (2016)
JOURNAL OF ORGANIC CHEMISTRY 81(6): 2308-2319.

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Abstract
Through a surprisingly nonregioselective oxidation process, the reaction of two analogous 2-hydroxy-substituted tribenzotriquinacenes (TBTQs) 8a/8b by o-iodoxybenzoic acid was found to afford the corresponding C-s- and C-1-symmetrical TBTQ-o-quinones 6a/6b and 7a/7b, respectively, in 1:1 ratio and excellent combined yields. This finding represents the first example of direct introduction of a functional group into a sterically hindered, inner bay-positions of a parent TBTQ skeleton. In contrast, the analogous reaction with 1-hydroxy-TBTQ 15 failed to produce the desired o-quinone 7a. After reduction of the quinones 6a and 7a to the corresponding catechols 17 and 23, electrophilic aromatic substitution could also be realized at the activated inner bay-position(s) to afford several tri- and tetrafunctionalized TBTQ compounds 18, 21, and 25. The C-s-symmetrical o-quinone 6a was converted into further single-wing extended derivatives such as TBTQ-based phenazines 27a-f, through condensation reactions, and to benzodioxine derivative 32 by Diels-Alder reaction with tetracyclone. The novel TBTQ: quinones and the corresponding TBTQ-catechols offer a variety of new accesses to single-wing-extended and functionalized TBTQ derivatives.
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Zhang Y-F, Tian W-F, Cao X-P, Kuck D, Chow H-F. o-Quinones Derived from Tribenzotriquinacenes: Functionalization of Inner Bay Positions and Use for Single-Wing Extensions. JOURNAL OF ORGANIC CHEMISTRY. 2016;81(6):2308-2319.
Zhang, Y. - F., Tian, W. - F., Cao, X. - P., Kuck, D., & Chow, H. - F. (2016). o-Quinones Derived from Tribenzotriquinacenes: Functionalization of Inner Bay Positions and Use for Single-Wing Extensions. JOURNAL OF ORGANIC CHEMISTRY, 81(6), 2308-2319.
Zhang, Y. - F., Tian, W. - F., Cao, X. - P., Kuck, D., and Chow, H. - F. (2016). o-Quinones Derived from Tribenzotriquinacenes: Functionalization of Inner Bay Positions and Use for Single-Wing Extensions. JOURNAL OF ORGANIC CHEMISTRY 81, 2308-2319.
Zhang, Y.-F., et al., 2016. o-Quinones Derived from Tribenzotriquinacenes: Functionalization of Inner Bay Positions and Use for Single-Wing Extensions. JOURNAL OF ORGANIC CHEMISTRY, 81(6), p 2308-2319.
Y.-F. Zhang, et al., “o-Quinones Derived from Tribenzotriquinacenes: Functionalization of Inner Bay Positions and Use for Single-Wing Extensions”, JOURNAL OF ORGANIC CHEMISTRY, vol. 81, 2016, pp. 2308-2319.
Zhang, Y.-F., Tian, W.-F., Cao, X.-P., Kuck, D., Chow, H.-F.: o-Quinones Derived from Tribenzotriquinacenes: Functionalization of Inner Bay Positions and Use for Single-Wing Extensions. JOURNAL OF ORGANIC CHEMISTRY. 81, 2308-2319 (2016).
Zhang, Yu-Fei, Tian, Wan-Fa, Cao, Xiao-Ping, Kuck, Dietmar, and Chow, Hak-Fun. “o-Quinones Derived from Tribenzotriquinacenes: Functionalization of Inner Bay Positions and Use for Single-Wing Extensions”. JOURNAL OF ORGANIC CHEMISTRY 81.6 (2016): 2308-2319.
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