Synthesis of 5,5-(Phenylmethylene)bis(2,2-butylidene-1,3-dioxane-4,6-dione) Derivatives without Catalyst in Water

doi:10.6023/cjoc201701046

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (9): 2449-2453.DOI: 10.6023/cjoc201701046 Previous Articles Next Articles

Notes

无催化剂、水相合成5,5-(苯基亚甲基)双(2,2-亚丁基-1,3-二噁烷-4,6-二酮)衍生物

张文锋^a, 许招会^a, 涂缘鸿^a, 廖传文b^b

a 江西师范大学化学化工学院南昌 330022;
b 江西省人民医院普外科南昌 330006

收稿日期:2017-01-23 修回日期:2017-04-13 发布日期:2017-04-27
通讯作者: 许招会 E-mail:gotoxzh@163.com
基金资助:
国家科技攻关计划（No.2001BA323C）和江西省研究生创新基金（No.YC2015-B023）资助项目.

Synthesis of 5,5-(Phenylmethylene)bis(2,2-butylidene-1,3-dioxane-4,6-dione) Derivatives without Catalyst in Water

Zhang Wenfeng^a, Xu Zhaohui^a, Tu Yuanhong^a, Liao Chuanwen^b

a Department of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022;
b Department of General Surgery, Jiangxi Province People's Hospital, Nanchang 330006

Received:2017-01-23 Revised:2017-04-13 Published:2017-04-27
Contact: 10.6023/cjoc201701046 E-mail:gotoxzh@163.com
Supported by:
Project supported by the National Science and Technology Project (No. 2001BA323C) and the Graduate Innovation Foundation of Jiangxi Province (No. YC2015-B023).

1. Synthesis of 5,5-(Phenylmethylene)bis(2,2-butylidene-1,3-dioxane-4,6-dione) Derivatives without Catalyst in Water.PDF(3059KB)

Abstract

A new simple and efficient synthesis of 5,5-(phenylmethylene)bis(2,2-butylidene-1,3-dioxane-4,6-dione) derivatives, based on aromatic aldehydes and 2,2-butylidene-1,3-dioxane-4,6-dione, via Tandem reaction of Knoevenagel condensation and Michael addition is described using water as solvent without catalyst. A variety of aromatic aldehydes were engaged in study and afforded respective products in high yields (63%~83%). The reaction has the advantages of mild conditions, simple operation and environmental friendliness.

Key words: aromatic aldehydes, tandem reaction, synthesis in water, catalyst-free

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Zhang Wenfeng, Xu Zhaohui, Tu Yuanhong, Liao Chuanwen. Synthesis of 5,5-(Phenylmethylene)bis(2,2-butylidene-1,3-dioxane-4,6-dione) Derivatives without Catalyst in Water[J]. Chin. J. Org. Chem., 2017, 37(9): 2449-2453.

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[1] Khan, K. M.; Maharvi, G. M.; Khan, M. T.; Shaikh, A. J. Bioorg. Med. Chem. 2006, 14, 344.
[2] Lipson, V. V.; Desenko, S. M.; Borodina, V. V.; Shirobokova, M. G.; Karnozhitskaya, T. M.; Musatov, V. I.; Kravchenko, S. V. Chem. Heterocycl. Compd. 2005, 41, 216.
[3] Lipson, V. V.; Svetlichnaya, N. V.; Shishkina, S. V.; Shishkin, O. V. Mendeleev Commun. 8, 18, 141.
[4] Lipson, V. V.; Borodina, V. V.; Shirobokova, M. G. Ukr. Khim. Zh. 2005, 71, 95.
[5] Strods, J.; Lielbriedis, I.; Neilands, O. Latv. PSR Zinatnu Akademijas Vestis, Kimijas Serija 1978, 2, 225.
[6] Trost, B. M.; Morris, P. J.; Sprague, S. J. J. Am. Chem. Soc. 2012, 134, 17823.
[7] King, F. E.; Felton, D. G. I. J. Chem. Soc. 1948, 13, 1371.
[8] Ramachary, D. B.; Kishor, M. J. Org. Chem. 2007, 12, 5056.
[9] Marco, B. A.; Manuel, T. A.; Itzia, P. M.; Francisco, M. M.; Georgina, E.; Elies, M.; Enrique, E. J. Chem. Crystallogr. 1999, 29, 759.
[10] Cravotto, G.; Demetri, A.; Nano, G. M.; Palmmisano, G.; Penoni, A.; Tagliapietra, S. Eur. J. Org. Chem. 2003, 2003, 4438.
[11] Hedge, J. W.; Kruse, C. W.; Snyder, H. R. J. Org. Chem. 1961, 26, 992.
[12] Shi, D.-Q.; Ni, S.-N.; Dou, G.-L. Chin. J. Org. Chem. 2009, 29, 788(in Chinese). (史达清, 倪赛男, 窦国兰, 有机化学, 2009, 29, 788.)
[13] Finguelli, F.; Pizzo, F.; Vaccaro, L. Synthesis 2000, 646.
[14] Labinger, J. A.; Herring, A. M.; Nercaw, J. E. J. Am. Chem. Soc. 1990, 112, 5628.
[15] Podgorsek, A.; Stavber, S.; Zupan, M.; Iskra, J. Green Chem. 2007, 11, 1212.
[16] Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. B. Angew. Chem., Int. Ed. 2005, 44, 257.
[17] Mori, Y.; Manabe, K.; Kobayashi, S. Angew Chem., Int. Ed. 2001, 40, 2815.
[18] Churruca, F.; SanMartin, R.; Dominguez, E. Synlett 2005, 3116.
[19] Yan, N.; Xiong, B.; Liao, W.-L.; Xu, Z.-H. Chin. J. Org. Chem. 2010, 30, 1391(in Chinese). (严楠, 熊斌, 廖维林, 许招会, 有机化学, 2010, 30, 1391.)
[20] Yu, J. J.; Wang, L. M.; Liu, J. Q.; Guo, F. L.; Liu, Y.; Jiao, N. Green Chem. 2010, 12, 216.
[21] Xu, Z.-H; Yan, N.; Liao, W.-L. J. Jiangxi Norm. Univ. (Nat. Sci.) 2012, 36, 524(in Chinese). (许招会, 严楠, 廖维林, 江西师范大学学报(自然科学版), 2012, 36, 524.)

无催化剂、水相合成5,5-(苯基亚甲基)双(2,2-亚丁基-1,3-二噁烷-4,6-二酮)衍生物

Synthesis of 5,5-(Phenylmethylene)bis(2,2-butylidene-1,3-dioxane-4,6-dione) Derivatives without Catalyst in Water

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