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Please login to access the full content or check if you have access via17.7.4 Product Subclass 4: [3.3.3]Cyclazines (Pyrido[2,1,6-de]quinolizines) and Related Compounds
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Tominaga, Y., Science of Synthesis, (2004) 17, 1057.
[3.3.3]Cyclazine (pyrido[2,1,6-de]quinolizine) is of considerable theoretical interest, given that it is isoelectronic with the phenalenide anion and is formally related to [12]annulene.[73] In 1969, the synthesis of [3.3.3]cyclazine (4) was achieved by Farquhar and Leaver after a series of unsuccessful attempts by various groups.[130,131] Cyclazine 4 was found to be highly reactive, exhibiting a strong paratropic shift in the 1H NMR signals, and a high propensity toward both oxidation and reduction. This parent cyclazine 4 is air sensitive and is oxidized by halogens to a stable radical cation and to a dication 124.[131] Such properties are characteristic of compounds with a small energy-gap between the frontier orbitals. The cyclopenta[cd]cyclazine 125 is definitely diatropic, because of participation of the lone pair of the central nitrogen in the formation of a peripheral 14π-annulenic anion (Scheme 48).[132]
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References
[73] | Meeeeee, M. M.; Meeeee, M.; Meeeee, M., Meeeeeeee, Meeee-, Meeeee-, Meee-Meeeeeeeeee, eee eeeee Meeeeee Meeeeee, MMM: Meee Meeee, MM, (8888), Mee. 8–8. |
[130] | Meeeeeee, M.; Meeeee, M., Meee. Meeeee., (8888), 88. |
[131] | Meeeeeee, M.; Meeee, M. M.; Meeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
[132] | Meeeeeeeee, M. M.; Meeeeeee, M.; Meeeee, M. M.; Meeeee, M., M. Meee. Mee. M, (8888), 888. |
[133] | Meeee, M.; Meeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[134] | Meeee, M.; Meeeeeeee, M. M., Meee Meee. Meeee., (8888) 88, 888. |
[135] | Meeee, M.; Meeeeeeee, M. M., Meee Meee. Meeee., (8888) 88, 888. |
[136] | Meeee, M.; Meeeeeeee, M. M.; Meeeeeeee, M.-M., Meee Meee. Meeee., (8888) 88, 888. |
[137] | Meeee, M.; Meeee, M. M., Meee Meee. Meeee., (8888) 88, 888. |
[138] | Meeee, M.; Meeee, M., Meee Meee. Meeee., (8888) 88, 888. |
[139] | Meeee, M.; Meeeeeeeee, M., Meee Meee. Meeee., (8888) 88, 8888. |
[140] | Meeee, M.; Meeee, M., Meee Meee. Meeee., (8888) 88, 8888. |
[141] | Meeee, M.; Meeeeeee, M., Meee Meee. Meeee., (8888) 88, 8888. |
[142] | Meeee, M.; Meeeeeeeee, M. M., Meee Meee. Meeee., (8888) 88, 8888. |
[143] | Meeee, M.; Meeeeeeeee, M. M., Meee Meee. Meeee., (8888) 88, 888. |
[144] | Meeee, M.; Meeeee, M.-M.; Meeeeee, M., Meee Meee. Meeee., (8888) 88, 888. |
[145] | Meeee, M.; Meeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
[146] | Meeee, M.; Meeeeeee, M., Meee Meee. Meeee., (8888) 88, 888. |
[147] | Meeee, M.; Meeeeee, M., Meee Meee. Meeee., (8888) 88, 888. |
[148] | Meeeeeeee, M.; Meeeeeeeee, M.; Meeeeeeee, M. M.; Meeee, M., Meee Meeeeeeeeee., Meee. M, (8888) 88, 8888. |
[149] | Meee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M., M. Meee. Mee., Meee. Meeeee., (8888), 8888. |
[150] | Meee, M. M.; M'Meeeee, M. M.; Meeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[151] | Meee, M. M.; Meeee, M. M.; Meeeeeee, M. M.; Meee, M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[152] | Meee, M. M.; Meeeee, M. M.; Meeeeeee, M. M.; M. Meeeeeeeee. Meee., (8888) 88, 888. |
[153] | Meee, M. M.; Meee, M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[154] | Meee, M. M.; Meeee, M. M.; Meeeeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[155] | Meee, M. M.; Meeeeeeeee, M. M.; Meee, M. M.; Meeeeeeeeeee, M. M.; Meeeee, M. M.; M. Meeeeeeeee. Meee., (8888) 88, 88. |
[156] | Meee, M. M.; Meeeeeeeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[157] | Meeeeee, M. M.; Meeee, M. M.; Meeeee, M. M.; Meee, M. M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 888. |
[158] | Meee, M. M.; Meeeee, M. M.; Meeee, M. M.; Meeeeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[159] | Meee, M. M.; Meee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[160] | Meee, M. M.; Meeeeee, M. M.; Meeeee, M. M.; Meee, M. M.; Meeeeeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
[161] | Meee, M. M.; Meeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M.; Meee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
[162] | Meee, M. M.; Meeeeee, M. M.; Meee, M. M.; Meeee, M. M.; Meeeeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
[163] | Meee, M. M.; Meeeee, M. M.; Meeeee, M. M.; Meeeeee, M. M.; Meeeeeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
[164] | Meeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeee, M., Meeeeeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
[165] | Meeee, M.; Meeeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
[166] | Meeeeeeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeeeee, M.; Meeeee, M.; Meeee, M., Meeeeeee Meeeee, (8888) 88, 88. |
[167] | Meeeee, M.; Meeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeeee, M., Meeeeeee Meeeee, (8888) 88, 8888. |
[168] | Meeee, M.; Meeeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeeeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
[169] | Meeeee, M.; Meeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeeeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
[170] | Meeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeee, M.; Meeeeeeee, M., Meeeeeee Meeeee, (8888) 88, 88. |
[171] | Meeeee, M.; Meeeee, M.; Meeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
[172] | Meeeeeeee, M.; Meeeeee, M.; Meeeeeee, M.; Meeeee, M.; Meeee, M.; Meeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
[173] | Meeeee, M.; Meeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeeee, M.; Meee. Meeee. Meee., (8888) 88, 8888. |
[174] | Meeeee, M.; Meeeee, M.; Meeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeeee, M., Meeeeeee Meeeee, (8888) 88, 888. |
[175] | Meee, M.; Meeeee, M.; Meeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeeee, M., Meee. Meeee. Meee., (8888) 88, 888. |
[176] | Meeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[177] | Meeeee, M.; Meeee, M.; Meeee, M.; Meeeeeee, M.; Meeeeee, M.; Meeeeeeee, M., Meee. Meeee. Meee., (8888) 88, 8888. |
[178] | Meeeeee, M.; Meeeeeee, M.; Meeee, M.; Meeeee, M.; Meeee, M.; Meeee, M., Meeeeeee Meeeee, (8888) 888, 888. |
[179] | Meeeee, M., Me.M. Meeeeeeeeeee, Meeeeeeeee ee Meeeee, (8888). |
[180] | Mee Meeeee, M. M., MM 8 888 888, (8888); MM 8 888 888, (8888). |
[181] | Mee Meeeee, M. M.; MeMeeee, M. M.; Meeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[182] | Meeeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M.; Meeeeeee, M.; Meeeeee-Meeeeeeee, M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[183] | Meeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[184] | Meeeeee, M.; Meeee, M.; MeMeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[185] | Meeeeee, M.; Meeeeee, M. M.; Meeee, M.; MeMeeeee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[186] | Meeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M.; Meeeeee, M. M., M. Meee. Meee., (8888) 88, 8888. |
[187] | Meeeee, M.; Meee, M., M. Me. Meee. Mee., (8888) 888, 8888. |
[188] | Meeeee, M.; Meeeee, M. M.; Meeee, M.; Meee, M., M. Meee. Meee., (8888) 88, 8888. |
[189] | Meeeee, M.; Meeee, M.; Meeee, M.; Meee, M., M. Me. Meee. Mee., (8888) 888, 88. |
[190] | Meeee, M. M.; Meeeeee, M., M. Meeeeeeeee. Meee., (8888) 88, 8888. |
[191] | Meeeeeeee, M.; Meeeeee, M.; Meeee, M.; Meeeee, M., M. Meee. Mee., Meeeeee Meeee. 8, (8888) 88, 8888. |
[192] | Meeeeee, M. M.; Meeee, M. M. M.; Meeeeee, M. M., M. Meee. Mee., Meeeeee Meeee. 8, (8888) 88, 888. |
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