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1 article(s) from Koçak, Ramazan

Synthesis of dibenzosuberenone-based novel polycyclic π-conjugated dihydropyridazines, pyridazines and pyrroles

Ramazan Koçak and
Arif Daştan

Beilstein J. Org. Chem. 2021, 17, 719–729, doi:10.3762/bjoc.17.61

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Graphical Abstract

Figure 1: Structures of dibenzosuberenone 1 and pyridazine and pyrrole derivatives.

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Figure 2: Structures of s-tetrazines 2a–l.

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Scheme 1: Inverse electron-demand Diels–Alder reactions of dibenzosuberenone (1) with tetrazines 2a–l.

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Scheme 2: Inverse electron-demand Diels–Alder reactions between dibenzosuberenone 1 and tetrazines 2k^a and 2l^b...

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Scheme 3: Proposed reaction mechanism for the formation of dibenzosuberenone derivatives 3 and 4.

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Scheme 4: Proposed mechanism for the formation of 5l.

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Scheme 5: Oxidation of dihydropyridazines 3a–f. All reactions were carried in CH₂Cl₂ at room temperature (4e:...

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Scheme 6: Synthesis of pyrrole 10a. ^a1.34 mmol 4a, Zinc (for 10aa: 6.68 mmol, for 10ab: 13.36 mmol), 10 mL gl...

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Scheme 7: Synthesis of pyrrole 10b. ^a1.21 mmol 4b, 12.10 mmol Zinc, 118 °C, 2 h. ^b1.13 mmol 10ba, 1.69 mmol K...

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Scheme 8: Synthesis of p-quinone methides 13–16. ^a1.77 mmol 11, 1.77 mmol 2, 5 mL toluene, 80 °C (13a: overni...

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Scheme 9: Proposed mechanism for the formation of 13.

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Figure 3: UV–vis spectra of 3c–f and 3k in CH₃CN at rt (c = 5 μM).

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Figure 4: Fluorescence spectra of 3c–f and 3k in CH₃CN at rt (c = 5 μM).

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Figure 5: Ambient (top) and fluorescence (bottom, under 365 nm UV light) images of 3c–f and 3k in CH₃CN.

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Published 15 Mar 2021

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