Strategy to Construct Functionalized Tetrazepine Derivatives via [4+3] Annulation Reaction of Azomethine Imine with Azadiene Precursor

doi:10.6023/cjoc202303031

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (9): 3180-3187.DOI: 10.6023/cjoc202303031 Previous Articles Next Articles

偶氮次甲基亚胺与氮杂二烯前体的[4+3]环加成反应构建功能化四氮杂䓬衍生物

张晓轲^a^,^c^,^*(), 郑相如^b, 王朝永^a^,^*()

a 重庆大学附属涪陵医院中心实验室重庆 408000
b 重庆医科大学附属第三医院重庆 401120
c 遵义医科大学贵州 563006

收稿日期:2023-03-21 修回日期:2023-05-15 发布日期:2023-06-06
基金资助:
贵州省科技厅基础研究计划(QKHJC-ZK[2023]-495); 重庆市自然科学基金(cstc2021jcyj-bsh0010)

Strategy to Construct Functionalized Tetrazepine Derivatives via [4+3] Annulation Reaction of Azomethine Imine with Azadiene Precursor

Xiaoke Zhang^a^,^c(), Xiangru Zheng^b, Chaoyong Wang^a()

a Central Laboratory, Chongqing University Fuling Hospital, Chongqing 408000
b The Third Affiliated Hospital of Chongqing Medical University, Chongqing 401120
c Zunyi Medical University, Guizhou 563006

Received:2023-03-21 Revised:2023-05-15 Published:2023-06-06
Contact: * E-mail: cqwchy@sina.com;xiaokezhang53@163.com
Supported by:
Guizhou Provincial Science and Technology Plan Program(QKHJC-ZK[2023]-495); Chongqing Natural Science Foundation(cstc2021jcyj-bsh0010)

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Abstract

Tetrazepine derivative exhibits good biological activities. Only a limited method has been devoted to constructing these frameworks to date. Therefore, an efficient and novel way was established for the synthesis of functionalized tetrazepine scaffolds through the cycloaddition reaction of azomethine imine with 1,2-azadiene formed in situ by α-halogeno hydrazones in the presence of KOH. This transformation shows excellent functional group tolerance and substrate scope.

Key words: α-halogeno hydrazone, azomethine imine, tetrazepine derivative, azadiene precursor

Cite this article

Xiaoke Zhang, Xiangru Zheng, Chaoyong Wang. Strategy to Construct Functionalized Tetrazepine Derivatives via [4+3] Annulation Reaction of Azomethine Imine with Azadiene Precursor[J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3180-3187.

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References 19

[1]	For some selected examples: (a) Hu X.; Li, D.; Chu, C.; Li, X.; Wang, X. H.; Jia, Y.; Hua, H. M.; Xu, F. X. Int. J. Mol. Sci. 2018, 19, 3403. doi: 10.3390/ijms19113403 pmid: 33793216
	(b) Xiao Y.; Gong Q.; Wang W. H.; Liu F.; Kong Q. H.; Pan F.; Zhang X. K.; Yu C. Y.; Hu S. S.; Fan F.; Li S. H.; Liu Y. Cancer Cell Int. 2020, 20, 371. doi: 10.1186/s12935-020-01463-w pmid: 33793216
	(c) Dong G. Q.; Liu Y.; Wu Y.; Tu J.; Chen S. Q.; Liu N.; Sheng C. Q. Chem. Commun. 2018, 54, 13535. doi: 10.1039/C8CC07810F pmid: 33793216
	(d) Fu D. J.; Li J.; Yu B. Eur. J. Med. Chem. 2021, 214, 113254. doi: 10.1016/j.ejmech.2021.113254 pmid: 33793216
	(e) Abdel-Halim M.; Sigler S.; Racheed N. A. S.; Hefnawy A.; Fathalla R. K.; Hammam M. A.; Maher A.; Maxuitenko Y. L.; Keeton A. B.; Hartmann R. W.; Engel M.; Piazza G. A.; Abadi A. H. J. Med. Chem. 2021, 64, 4462. doi: 10.1021/acs.jmedchem.0c01120 pmid: 33793216
[2]	(a) Krueger B. W.; Fischer R.; Bertram H. J.; Bretschneider T.; Boehm S.; Krebs A.; Schenke T.; Santel H. J.; Lurssen K.; Schmidt R. R.; Erdelen C.; Wachendorff-Neumann U.; Stendel, W. EP0508126, 1992.
	(b) Muehlebach M.; Cederbaum F.; Cornes D.; Friedmann A. A.; Glock J.; Hall G.; Indolese A. F.; Kloer D. P.; Goupil G. L.; Maetzke T.; Meier H.; Schneider R.; Stoller A.; Szczepanski H.; Wendeborna S.; Widmer H. Pest. Manage. Sci. 2011, 67, 1499. doi: 10.1002/ps.v67.12
	(c) Kamata M.; Yamashita T.; Tokkyo Koho, J. K. JP 2009196966, 2009.
	(d) Kamata M.; Yamashita T.; Kina A.; Tawada M.; Endo S.; Mizukami A.; Sasaki M.; Tani A.; Nakano Y.; Watanabe Y.; Furuyama N.; Funami M.; Amano N.; Fukatsu K. Bioorg. Med. Chem. Lett. 2012, 22, 4769. doi: 10.1016/j.bmcl.2012.05.062
[3]	(a) Kodato S. I.; Wada H.; Saito S.; Takeda M.; Nishibata Y.; Aoe K.; Date T.; Onoda Y.; Tamaki H. Chem. Pharm. Bull. 1987, 35, 80. doi: 10.1248/cpb.35.80
	(b) Mashevskaya I. V.; Makhmudov R. R.; Kuslina L. V.; Mokrushin I. G.; Shurov S. N.; Maslivets A. N. Pharm. Chem. J. 2012, 45, 660. doi: 10.1007/s11094-012-0697-0
	(c) Ibrahim S. M.; Baraka M. M.; El-Sabbagh O. I.; Kothayer H. Med. Chem. Res. 2013, 22, 1488. doi: 10.1007/s00044-012-0102-2
[4]	Almerico A. M.; Mingoia F.; Diana P.; Barraja P.; Lauria A.; Montalbano A.; Cirrincione G.; Dattolo G. J. Med. Chem. 2005, 48, 2859. pmid: 15828824
[5]	(a) Gupta C. M.; Bhaduri A. P.; Khanna N. M. J. Med. Chem. 1968, 11, 392. pmid: 5663640
	(b) Ghorab M. M.; Heiba H. I.; El-gawish M. A. Phosphorus, Sulfur Silicon Relat. Elem. 1995, 106, 85. doi: 10.1080/10426509508027893 pmid: 5663640
	(c) Hamama W. S.; El-Bana G. G.; Shaaban S.; Zoorob H. H. J. Heterocycl. Chem. 2018, 55, 971. doi: 10.1002/jhet.v55.4 pmid: 5663640
[6]	(a) Maggio B.; Raffa D.; Raimondi M. V.; Cascioferro S.; Plescia F.; Tolomeo M.; Barbusca E.; Cannizzo G.; Mancuso S.; Daidone G. Eur. J. Med. Chem. 2008, 43, 2386. doi: 10.1016/j.ejmech.2008.01.007
	(b) Maggio B.; Raffa D.; Raimondi M. V. ARKIVOC 2006, xv, 120.
	(c) Vahedi H.; Rajabzadeh G.; Farvandi F. Chin. Chem. Lett. 2010, 21, 1419. doi: 10.1016/j.cclet.2010.07.006
	(d) Darehkordi A.; Khorasani F. N.; Mohammadi M.; Kazemi E. Monatsh. Chem. 2020, 151, 1835. doi: 10.1007/s00706-020-02703-5
[7]	For selected examples, see: (a) Zhou M. B.; Song, R. J.; Wang, C. Y.; Li, J. H. Angew. Chem., Int. Ed. 2013, 52, 10805. doi: 10.1002/anie.201304902
	(b) Feng J. J.; Lin T. Y.; Wu H. H.; Zhang J. L. J. Am. Chem. Soc. 2015, 137, 3787. doi: 10.1021/jacs.5b01305
	(c) Liu L. L.; Chiu P. Chem. Commun. 2011, 47, 3416. doi: 10.1039/c1cc00087j
	(d) Gao H. Y.; Wu X. X.; Zhang J. L. Chem. Commun. 2010, 46, 8764. doi: 10.1039/c0cc02778b
[8]	Kumari Y. B. Heterocycl. Commun. 2007, 13, 177.
[9]	Li Z. F.; Li S. K.; Kan T. J.; Wang X. Y.; Xin X.; Hou Y. L.; Gong P. Adv. Synth. Catal. 2020, 362, 2626. doi: 10.1002/adsc.v362.13
[10]	(a) Huisgen R.; Fleischmann R.; Eckell A. Tetrahedron Lett. 1960, 1, 1.
	(b) Breugst M.; Reissig H. U. Angew. Chem., Int. Ed. 2020, 59, 12293. doi: 10.1002/anie.v59.30
	(c) Yue G. Z.; Liu B. Chin. J. Org. Chem. 2020, 40, 3132. (in Chinese) doi: 10.6023/cjoc202005092
	(乐贵洲, 刘波, 有机化学, 2020, 40, 3132.) doi: 10.6023/cjoc202005092
[11]	(a) Bakthadoss M.; Agarwal V. ChemistrySelect 2018, 3, 6960. doi: 10.1002/slct.v3.24
	(b) Choi A.; Castle J.; Saruengkhanphasit R.; Coldham I. Synthesis 2020, 1273.
	(c) Sandmeier T.; Sievertsen N.; Carreira E. M. Helv. Chim. Acta 2020, 103, e2000058. doi: 10.1002/hlca.v103.6
[12]	(a) Li Z.; Yu H.; Liu Y.; Zhou L.; Sun Z.; Guo H. Adv. Synth. Catal. 2016, 358, 1880. doi: 10.1002/adsc.v358.12 pmid: 29215289
	(b) Zhou L.; Yuan C.; Zhang C.; Zhang L.; Gao Z.; Wang C.; Liu H.; Wu Y.; Guo H. Adv. Synth. Catal. 2017, 359, 2316. doi: 10.1002/adsc.v359.13 pmid: 29215289
	(c) Zhu C. Z.; Feng J. J.; Zhang J. Chem. Commun. 2017, 53, 4688. doi: 10.1039/C7CC02078C pmid: 29215289
	(d) Yu L.; Zhong Y.; Yu J.; Gan L.; Cai Z.; Wang R.; Jiang X. Chem. Commun. 2018, 54, 2353. doi: 10.1039/C7CC09640B pmid: 29215289
	(e) Cheng X.; Cao X.; Xuan J.; Xiao W. J. Org. Lett. 2018, 20, 52. doi: 10.1021/acs.orglett.7b03344 pmid: 29215289
[13]	(a) Wei L.; Wang Z. F.; Yao L.; Qiu G. F.; Tao H. Y.; Li H.; Wang C. J. Adv. Synth. Catal. 2016, 358, 3955. doi: 10.1002/adsc.v358.24
	(b) Wang Y. F.; Zhu L. P.; Wang M. R.; Xiong J.; Chen N. N.; Feng X.; Xu Z. Q.; Jiang X. X. Org. Lett. 2018, 20, 6506. doi: 10.1021/acs.orglett.8b02828
[14]	(a) Li Z.; Feng Y. L.; Hou Z. F.; Zhang L.; Yang W. J.; Wu Y.; Xiao Y. M.; Guo H. C. RSC Adv. 2015, 5, 34481. doi: 10.1039/C5RA04374C
	(b) Mei G. J.; Zhu Z. Q.; Zhao J. J.; Bian C. Y.; Chen J.; Chen R. W.; Shi F. Chem. Commun. 2017, 53, 2768. doi: 10.1039/C6CC09775H
	(c) Li C.; Wang C. S.; Li T. Z.; Mei G. J.; Shi F. Org. Lett. 2019, 21, 598. doi: 10.1021/acs.orglett.8b03604
	(d) Yuan C. H.; Zhou L. J.; Xia M. R.; Sun Z. H.; Wang D. Q.; Guo H. C. Org. Lett. 2016, 18, 5644. doi: 10.1021/acs.orglett.6b02885
	(e) Na R.; Jing C.; Xu Q.; Jiang H.; Wu X.; Shi J. J. Am. Chem. Soc. 2011, 133, 13341.
	(f) Wang M.; Huang Z. J.; Xu J. F.; Chi Y. R. J. Am. Chem. Soc. 2014, 136, 1214. doi: 10.1021/ja411110f
	(g) Na R.; Jing C. F.; Xu Q. H.; Jiang H.; Wu X.; Shi J. Y.; Zhong J. C.; Wang M.; Benitez D.; Tkatchouk E.; Goddard W. A.; Guo H. C.; Kwon O. J. Am. Chem. Soc. 2011, 133, 13337. doi: 10.1021/ja200231v
	(h) Hu X. Q.; Chen J. R.; Gao S.; Feng B.; Lu L. Q.; Xiao W. J. Chem. Commun. 2013, 49, 7905. doi: 10.1039/c3cc43888k
	(i) Yang W. J.; Yuan C. H.; Liu Y.; Mao B. M.; Sun Z. H.; Guo H. C. J. Org. Chem. 2016, 81, 7597. doi: 10.1021/acs.joc.6b01296
[15]	(a) Jin Q.; Zhang J.; Jiang C.; Zhang D.; Gao M.; Hu S. J. Org. Chem. 2018, 83, 8410. doi: 10.1021/acs.joc.8b01055
	(b) Hu X. Q.; Chen J. R.; Gao S.; Feng B.; Lu L. Q.; Xiao W. J. Chem. Commun. 2013, 49, 7906.
	(c) Zhi Y.; Zhao K.; Shu T.; Enders D. Synthesis 2016, 48, 240.
	(d) Chen L.; Yang G. M.; Wang J.; Jia Q. F.; Wei J.; Du Z. Y. RSC Adv. 2015, 5, 76697.
[16]	For selected examples, see: (a) Zhang X. K.; Pan, Y.; Wang, H. B.; Liang, C.; Ma, X. F.; Jiao, W.; Shao, H. W. Adv. Synth. Catal. 2021, 363, 459. doi: 10.1002/adsc.v363.2 pmid: 26974596
	(b) Chen J. R.; Dong W. R.; Candy M.; Pan F. F.; Jörres M.; Bolm C. J. Am. Chem. Soc. 2012, 134, 6924. doi: 10.1021/ja301196x pmid: 26974596
	(c) Huang R.; Chang X.; Li J.; Wang C. J. J. Am. Chem. Soc. 2016, 138, 3998. doi: 10.1021/jacs.6b01008 pmid: 26974596
	(d) Quan B. X.; Zhuo J. R.; Zhao J. Q.; Zhang M. L.; Zhou M. Q.; Zhang X. M.; Yuan W. C. Org. Biomol. Chem. 2020, 18, 1886. doi: 10.1039/C9OB02733E pmid: 26974596
	(f) Chen B.; Chu W. D.; Liu Q. Z. RSC Adv. 2019, 9, 1487. doi: 10.1039/c8ra08909d pmid: 26974596
	(g) Huang R.; Chang X.; Li J.; Wang C. J. J. Am. Chem. Soc. 2016, 138, 3998. doi: 10.1021/jacs.6b01008 pmid: 26974596
	(h) Yin W. H.; Fang L.; Wang Z. Y.; Gao F.; Li Z. F.; Wang Z. Y. Org. Lett. 2020, 21, 7361. doi: 10.1021/acs.orglett.9b02661 pmid: 26974596
	(i) Cao W. B.; Xu X. P.; Ji S. J. Org. Biomol. Chem. 2017, 15, 1651. doi: 10.1039/C6OB02362B pmid: 26974596
	(j) Zhong X. G.; Lv J.; Luo S. Org. Lett. 2015, 17, 1561. doi: 10.1021/acs.orglett.5b00445 pmid: 26974596
	(k) Deng Y. M.; Pei C.; Arman H.; Dong K. Y.; Xu X. F.; Doyle M. P. Org. Lett. 2016, 18, 5884. doi: 10.1021/acs.orglett.6b02965 pmid: 26974596
[17]	Zhao H. W.; Pang H. L.; Tian T.; Li B.; Chen X. Q.; Song X. Q.; Meng W.; Yang Z.; Liu Y. Y.; Zhao Y. D. Adv. Synth. Catal. 2016, 358, 1826. doi: 10.1002/adsc.201600093
[18]	Cheng B.; Li Y. T.; Wang T. M.; Zhang X. P.; Li H.; Li Y.; Zhai H. B. Chem. Commun. 2019, 55, 14606. doi: 10.1039/C9CC08326J
[19]	Zhang X. K.; Wang H. B.; Li Z. W.; Shu Y.; Gan S. Zhang X. F.; Shao H. W.; Wang C. Y. ACS Omega 2022, 7, 40963. doi: 10.1021/acsomega.2c04127

Entry	Base	Solvent	Yield^b/%
1	Na₂CO₃	CH₂Cl₂	36
2	Cs₂CO₃	CH₂Cl₂	51
3	K₂CO₃	CH₂Cl₂	73
4	Na₂CO₃	CH₂Cl₂	64
5	KOH	CH₂Cl₂	79
6	KO^tBu	CH₂Cl₂	42
7	TEDA	CH₂Cl₂	Trace
8	TEA	CH₂Cl₂	Trace
9	KOH	Et₂O	57
10	KOH	CHCl₃	72
11	KOH	MeCN	75
12	KOH	DMF	63
13	KOH	THF	91
14	KOH	EtOAc	60
15^c	KOH	THF	56
16^d	KOH	THF	89

Entry	Base	Solvent	Yield^b/%
1	Na₂CO₃	CH₂Cl₂	36
2	Cs₂CO₃	CH₂Cl₂	51
3	K₂CO₃	CH₂Cl₂	73
4	Na₂CO₃	CH₂Cl₂	64
5	KOH	CH₂Cl₂	79
6	KO^tBu	CH₂Cl₂	42
7	TEDA	CH₂Cl₂	Trace
8	TEA	CH₂Cl₂	Trace
9	KOH	Et₂O	57
10	KOH	CHCl₃	72
11	KOH	MeCN	75
12	KOH	DMF	63
13	KOH	THF	91
14	KOH	EtOAc	60
15^c	KOH	THF	56
16^d	KOH	THF	89

偶氮次甲基亚胺与氮杂二烯前体的[4+3]环加成反应构建功能化四氮杂䓬衍生物

Strategy to Construct Functionalized Tetrazepine Derivatives via [4+3] Annulation Reaction of Azomethine Imine with Azadiene Precursor

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