Different Pathways for the Cyclocondensation Reactions of 1,2-Diamine and 1,2-Diketone†

doi:10.7503/cjcu20180302

Abstract

Abstract:

It is generally acknowledged that in protic organic solvents, 1,2-diamine reacts with 1,2-diketone to form an aromatic compound containing the pyrazine ring. As expected, the condensation reactions of 1,4-bis-[(triisopropylsilyl)ethynyl]naphthalene-2,3-diamine or 1,4-bis[(triisopropylsilyl)ethynyl]anthracene-2,3-diamine with 3,5-di-tert-butyl-1,2-benzoquinone yielded diazatetracene and diazapentacene derivatives. Meanwhile, naphthoazepin and anthroazepin derivatives which contained the imidazole ring were also obtained. Naphthoazepin and anthroazepin derivatives contained a seven-membered ring. All new compounds were characterized by proton and carbon-13 nuclear magnetic resonance spectroscopy, UV-vis spectrophotometry, high resolution mass spectrometry and single crystal X-ray diffraction. The possible reaction mechanisms were proposed as well.

Key words: Azacene, Cyclo-condensation reaction, Ring expansion, Organic semiconductor, Single-crystal structure

CLC Number:

O626.4

TrendMD:

ZHU Lei,HAN Junyan,CHANG Haizhen,QIU Yuyuan,ZHANG Yanan,PENG Danni,HU Wei,MIAO Shaobin. Different Pathways for the Cyclocondensation Reactions of 1,2-Diamine and 1,2-Diketone^†[J]. Chem. J. Chinese Universities, 2018, 39(12): 2686.

Figures/Tables 9

References 28

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Compd.	Molucular formula	Appearance	Yield(%)	HRMS, m/z[M]⁺	UV-Vis(CH₂Cl₂), λ_abs/nm
1a	C₄₆H₆₆N₂Si₂	Dark red solid	45	702.4766	294, 320, 336, 414, 486, 520, 558
2a	C₄₆H₆₆N₂Si₂O	Yellow solid	5	718.4763	330, 398
1b	C₅₀H₆₈N₂Si₂	Dark greed solid	8	752.4950	246, 305, 320, 358, 444, 576, 624, 678
2b	C₅₀H₆₈N₂Si₂O	Rose red solid	15	768.4902	288, 320, 344, 397, 421, 494

Compd.	Molucular formula	Appearance	Yield(%)	HRMS, m/z[M]⁺	UV-Vis(CH₂Cl₂), λ_abs/nm
1a	C₄₆H₆₆N₂Si₂	Dark red solid	45	702.4766	294, 320, 336, 414, 486, 520, 558
2a	C₄₆H₆₆N₂Si₂O	Yellow solid	5	718.4763	330, 398
1b	C₅₀H₆₈N₂Si₂	Dark greed solid	8	752.4950	246, 305, 320, 358, 444, 576, 624, 678
2b	C₅₀H₆₈N₂Si₂O	Rose red solid	15	768.4902	288, 320, 344, 397, 421, 494

Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(101 MHz, CDCl₃), δ
1a	8.80—8.78(m, 1H), 8.75—8.72(m, 1H), 7.97(s, 1H), 7.80(s, 1H), 7.64—7.62(m, 2H), 1.83(s, 9H, CH₃), 1.48(s, 9H, CH₃), 1.38—1.27[m, 42H, CH(CH₃)₂]	153.94, 148.38, 146.04, 143.33, 140.59, 139.49, 135.67, 135.09, 127.94, 127.92, 127.80, 127.76, 127.24, 123.34, 121.01, 120.60, 107.85, 107.11, 103.93, 103.47, 37.50, 35.92, 31.62, 30.71, 19.25
2a	8.82(d,J=8.0 Hz, 1H), 8.60(d, J=8.0 Hz, 1H), 7.59(m, 2H), 7.20(s, 1H), 6.86(s, 1H), 1.51(s, 9H, CH₃), 1.32(s, 9H, CH₃), 1.27—1.20[m, 42H, CH(CH₃)₂]	165.40, 152.90, 146.11, 145.88, 133.08, 131.97, 131.87, 127.79, 127.13, 126.71, 125.99, 125.66, 117.62, 114.02, 111.53, 109.54, 105.68, 104.39, 101.94, 101.69, 39.14, 37.33, 30.66, 29.59, 18.91, 18.88, 11.86
1b	9.49(s, 1H), 9.40(s, 1H), 8.04(d,J=7.1 Hz, 1H), 7.99(d, J=7.1 Hz, 1H), 7.89(s, 1H), 7.74(s, 1H), 7.47(m, 2H), 1.83(s, 9H, CH₃), 1.48(s, 9H, CH₃), 1.42—1.34[m, 42H, CH(CH₃)₂]	154.06, 148.30, 146.34, 143.77, 140.33, 139.29, 132.99, 132.90, 132.85, 132.51, 128.89, 128.86, 127.39, 127.06, 126.85, 126.74, 126.71, 123.27, 120.73, 120.22, 109.06, 108.37, 104.76, 104.23, 37.39, 35.84, 31.47, 30.49, 19.24, 19.20, 11.94, 11.90
2b	9.47(s, 1H), 9.24(s, 1H), 8.03(m, 2H), 7.50(d,J=7.2 Hz, 2H), 7.19(s, 1H), 6.87](s, 1H), 1.53(s, 9H, CH₃), 1.35—1.30[m, 51H, CH₃, CH(CH₃)₂]	165.47, 154.14, 153.83, 146.68, 146.60, 133.07, 131.89, 131.61, 131.16, 130.26, 128.43, 128.32, 126.34, 126.01, 125.95, 125.85, 125.83, 117.82, 111.07, 110.73, 105.39, 105.06, 102.61, 102.34, 39.41, 37.65, 29.76, 19.23, 19.18, 12.10, 11.84

Compd.	¹H NMR(400 MHz, CDCl₃), δ	¹³C NMR(101 MHz, CDCl₃), δ
1a	8.80—8.78(m, 1H), 8.75—8.72(m, 1H), 7.97(s, 1H), 7.80(s, 1H), 7.64—7.62(m, 2H), 1.83(s, 9H, CH₃), 1.48(s, 9H, CH₃), 1.38—1.27[m, 42H, CH(CH₃)₂]	153.94, 148.38, 146.04, 143.33, 140.59, 139.49, 135.67, 135.09, 127.94, 127.92, 127.80, 127.76, 127.24, 123.34, 121.01, 120.60, 107.85, 107.11, 103.93, 103.47, 37.50, 35.92, 31.62, 30.71, 19.25
2a	8.82(d,J=8.0 Hz, 1H), 8.60(d, J=8.0 Hz, 1H), 7.59(m, 2H), 7.20(s, 1H), 6.86(s, 1H), 1.51(s, 9H, CH₃), 1.32(s, 9H, CH₃), 1.27—1.20[m, 42H, CH(CH₃)₂]	165.40, 152.90, 146.11, 145.88, 133.08, 131.97, 131.87, 127.79, 127.13, 126.71, 125.99, 125.66, 117.62, 114.02, 111.53, 109.54, 105.68, 104.39, 101.94, 101.69, 39.14, 37.33, 30.66, 29.59, 18.91, 18.88, 11.86
1b	9.49(s, 1H), 9.40(s, 1H), 8.04(d,J=7.1 Hz, 1H), 7.99(d, J=7.1 Hz, 1H), 7.89(s, 1H), 7.74(s, 1H), 7.47(m, 2H), 1.83(s, 9H, CH₃), 1.48(s, 9H, CH₃), 1.42—1.34[m, 42H, CH(CH₃)₂]	154.06, 148.30, 146.34, 143.77, 140.33, 139.29, 132.99, 132.90, 132.85, 132.51, 128.89, 128.86, 127.39, 127.06, 126.85, 126.74, 126.71, 123.27, 120.73, 120.22, 109.06, 108.37, 104.76, 104.23, 37.39, 35.84, 31.47, 30.49, 19.24, 19.20, 11.94, 11.90
2b	9.47(s, 1H), 9.24(s, 1H), 8.03(m, 2H), 7.50(d,J=7.2 Hz, 2H), 7.19(s, 1H), 6.87](s, 1H), 1.53(s, 9H, CH₃), 1.35—1.30[m, 51H, CH₃, CH(CH₃)₂]	165.47, 154.14, 153.83, 146.68, 146.60, 133.07, 131.89, 131.61, 131.16, 130.26, 128.43, 128.32, 126.34, 126.01, 125.95, 125.85, 125.83, 117.82, 111.07, 110.73, 105.39, 105.06, 102.61, 102.34, 39.41, 37.65, 29.76, 19.23, 19.18, 12.10, 11.84

Compound	2a	β/(°)	90.813(3)
Chemical formula	C₄₆H₆₆N₂Si₂O	γ/(°)	91.979(2)
Formula weight	719.19	V/nm³	4.4174(2)
Crystal system	Triclinic	Z value	4
Space group	P1	T/K	150(2)
a/nm	1.44303(4)	No. obsd[I>2σ(I)]	15314
b/nm	1.48385(4)	No. parameter	955
c/nm	2.13227(8)	Goodness of fit GOF^*	1.032
α/(°)	104.449(3)	Residuals^a, R₁, wR₂	0.0514, 0.1430