Citation: Hanan A. Soliman, Tarek A. Salama. Silicon-mediated highly efficient synthesis of 1, 8-dioxo-octahydroxanthenes and their transformation to novel functionalized pyrano-tetrazolo [1, 5-a] azepine derivatives[J]. Chinese Chemical Letters, ;2013, 24(05): 404-406. shu

Silicon-mediated highly efficient synthesis of 1, 8-dioxo-octahydroxanthenes and their transformation to novel functionalized pyrano-tetrazolo [1, 5-a] azepine derivatives

Hanan A. Soliman ^a ,
Tarek A. Salama ^b,,

1.
a Photochemistry Department, National Research Center, Dokki, Cairo 12622, Egypt;
2.
b Chemistry Department, Faculty of Science, Mansoura University, Mansoura 35516, Egypt

Corresponding author: Tarek A. Salama,
Received Date: 11 January 2013
Available Online: 5 March 2013

A facile and highly efficient protocol for the synthesis of 1,8-dioxo-octahydroxanthene derivatives was achieved through cascade Knoevenagel-Michael condensations and cyclo-dehydration reaction utilizing tetrachlorosilane (TCS) as catalyst under mild conditions. Reaction of the titled compounds with TCS-NaN₃ to give novel functionalized pyrano[3,2-c]tetrazolo[1,5-a]azepine derivatives is also described.
- Tetrachlorosilane,
- 1,8-Dioxo-octahydroxanthenes,
- Synthesis,
- Tetrazolo[1,5-a]azepines
1. [1]
  [1] S. Hatakeyma, N. Ochi, H. Numata, et al., A new route to substituted 3-methoxycarbonyldihydropyrans: enantioselective synthesis of (-)-methyl elenolate, J. Chem. Soc. Chem. Commun. 1988 (17) (1988) 1202-1204.
2. [2]
  [2] O. Sirkecioglu, N. Talinli, A. Akar, Chemical aspects of santalin as a histological stain, J. Chem. Res. (S) (1995) 502-506.
3. [3]
  [3] J.P. Poupelin, G. Saint-Rut, O. Foussard-Blanpin, Synthesis and anti-inflammatory properties of bis(2-hydroxy-1-naphthyl)methane derivatives. I. Monosubstituted derivatives, Eur. J. Med. Chem. 13 (1978) 67-71.
4. [4]
  [4] J.F. Callan, P. De Silva, D.C. Magri, Luminescent sensors and switches in the early 21st century, Tetrahedron 61 (2005) 8551-8588.
5. [5]
  [5] G.P. Ellis, The chemistry of heterocyclic compounds, in: A. Weissberger, E.C.E. Tylor (Eds.), Chromene, Chromanes and Chromone, John Wiley, New York, 1977, p. 13.
6. [6]
  [6] A. Banerjee, A.K. Mukherjee, Chemical aspects of santalin as a histological stain, Stain Technol. 56 (1981) 83-85.
7. [7]
  [7] (a) D.Q. Shi, Y.H.Wang, Z.S. Lu, et al., Condensation of aromatic aldehydeswith acidic methylene compounds without catalyst, Synth. Commun. 30 (2000) 713-726;
8. [8]
  (b) T.S. Jin, J.S. Zang, A.Q. Wang, et al., Solid-state condensation reactions between aldehydes and 5,5-dimethyl 1,3-cyclohexanedione by grinding at roomtemperature, Synth. Commun. 35 (2005) 2339-2345;
9. [9]
  (c) B. Das, P. Thirupathi, K. Ravinder Reddy, et al., An efficient synthesis of 1,8-dioxooctahydroxanthenes using heterogeneous catalyst, Catal. Commun. 8 (2007) 535-538;
10. [10]
  (d) T.S. Jin, J.S. Zang, J.C. Xiao, et al., Clean synthesis of 1,8-dioxo-octahydroxanthene derivatives catalyzed by p-dodocylbenzenesulfonic acid in aqueous media, Synlett 2004 (5) (2004) 866-870;
11. [11]
  (e) T.S. Jin, J.S. Zang, A.Q. Wang, et al., Ultrasound-assisted synthesis of 1,8-dioxooctahydroxanthene derivatives catalyzed by p-dodocylbenzenesulfonic acid in aqueous media, Ultrason. Sonochem. 13 (2006) 220-224;
12. [12]
  (f) A. Llangovan, S. Malayappasamy, S. Mularidharan, et al., A highly efficient green synthesis of 1,8-dioxo-octahydroxanthenes, Chem. Central J. 5 (2011) 81, http://dx.doi.org/10.1186/1752-153X-5-81 and references cited therein;
13. [13]
  (g) S. Kantevari, R. Bantu, L. Nagarapu, HClO₄-SiO₂ and PPA-SiO₂ catalyzed efficient one-pot Knoevenagel condensation,Micheal addition and cyclodehydration of dimedone and aldehydes in acetonitrile, aqueous and solvent free condition: scope and limitations, J. Mol. Catal. A: Chem. 269 (2007) 53-57.
14. [14]
  [8] For a review, J.R. Herr, 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods, Bioorg. Med. Chem. 10 (2002) 3379-3393.
15. [15]
  [9] B.C. May, A.D. Abell, a-Methylene tetrazole-based peptidomimetics: synthesis and inhibition of HIV protease, J. Chem. Soc. Perkin Trans. 1 (2002) 172-178.
16. [16]
  [10] K. Nonoshita, Y. Ogino, M. Ishikawa, et al., PCT Int. Appl. WO₂004-JP19843, 2005; Chem. Abstr. 143 (2005) 153371.
17. [17]
  [11] M. Seki, Y. Tarao, K. Yamada, et al., PCT Int. Appl. WO 2005-JP2974, 2005; Chem. Abstr. 143 (2005) 266938.
18. [18]
  [12] Z. Miao, Y. Sun, S. Nakajima, et al., U.S. Pat. Appl. US 2005 153877, 2005; Chem. Abstr. 143 (2005) 153709.
19. [19]
  [13] B.J. Al-Hourani, S.K. Sharma, M. Suresh, et al., Novel 5-substitutd 1H-tetrazoles as cyclooxygenase-2 (COX-2) inhibitors, Bioorg. Med. Chem. Lett. 22 (2012) 2235-2238.
20. [20]
  [14] T.A. Salama, M.A. Ismail, A.M. Khalil, et al., Silicon-assisted O-heterocyclic synthesis: mild and efficient one-pot syntheses of E-3-benzylideneflavanones, coumarin-3-carbonitriles/carboxamides, and benzannulated spiropyran derivatives, ARKIVOC ix (2012) 242-253.
21. [21]
  [15] T.A. Salama, Z. Novak, N-Halosuccinimide/SiCl₄ as mild and efficient systems for the a-mono-halogenation of carbonyl compounds and for benzylic halogenation, Tetrahedron Lett. 52 (2011) 4026-4029.
22. [22]
  [16] T.A. Salama, A.S. El-Ahl, S.S. Elmorsy, et al., A new convenient procedure for the thionation of carbonyl compounds utilizing tetrachlorosilane-sodium sulfide, Tetrahedron Lett. 50 (2009) 5933-5936.
23. [23]
  [17] T.A. Salama, S.S. Elmorsy, A.M. Khalil, et al., A SiCl₄-ZnCl₂ induced general, mild and efficient one-pot, three-component synthesis of β-amido ketone libraries, Tetrahedron Lett. 48 (2007) 6199-6203.
24. [24]
  [18] T.A. Salama, S.S. Elmorsy, A.M. Khalil, SiCl₄-Zn Induced reductive coupling of carbonyl compounds: novel and efficient routes for one-pot syntheses of 1,2,3-triarylpropen-2-ones and pinacolones at room temperature, Tetrahedron Lett. 48 (2007) 4395-4398.
25. [25]
  [19] T.A. Salama, S.S. Elmorsy, A.M. Khalil, et al., Novel uncatalyzed hydrocyanation of ketones utilizing tetrachlorosilane-potassium cyanide reagent, Synth. Commun. 37 (2007) 1313-1319.
26. [26]
  [20] T.A. Salama, S.S. Elmorsy, A.M. Khalil, et al., Silicon-mediated direct conversion of acyl chlorides to carbamoyl azides or/and tetrazolinones under mild conditions, Chem. Lett. 40 (2011) 1149-1151.
27. [27]
  [21] T.A. Salama, S.S. Elmorsy, Silicon-mediated synthesis and selected transformations of b-chloroketones, Chin. Chem. Lett. 22 (2011) 1171-1174.
28. [28]
  [22] T.A. Salama, A.S. El-Ahl, A.M. Khalil, et al., A convenient regiospecific synthesis of new conjugated tetrazole derivatives via the reaction of dienones with the tetrachlorosilane-sodium azide reagent and their NMR structural assignment, Monatsh. Chem. 134 (2003) 1241-1252.
29. [29]
  [23] A.S. El-Ahl, S.S. Elmorsy, H.A. Soliman, et al., A facile and convenient synthesis of substituted tetrazole derivatives from ketones or α,β-unsaturated ketones, Tetrahedron Lett. 36 (1995) 7337-7340.
30. [30]
  [24] A. Vinkatesham, R. Sirinivasa Rao, K. Nagaiah, et al., Synthesis of new chromenoannulated cis-fused pyrano[3,4-c]pyran derivatives via domino Knoevenagelhetero-Diels-Alder reactions and their biological evaluation towards antiproliferative activity, Med. Chem. Commun. 3 (2012) 652-658.
31. [31]
  [25] F. Fernandez, W. Morishita, E. Zuniga, et al., Pharmacotherapy for cognitive impairment in a mouse model of Down syndrome, Nat. Neurosci. 10 (2007) 411-413.
1. [1]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
2. [2]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
3. [3]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
4. [4]
  Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
5. [5]
  Shaonan Liu , Shuixing Dai , Minghua Huang . The impact of ester groups on 1,8-naphthalimide electron transport material in organic solar cells. Chinese Journal of Structural Chemistry, 2024, 43(6): 100277-100277. doi: 10.1016/j.cjsc.2023.100277
6. [6]
  Zhiwei Chen , Heyun Sheng , Xue Li , Menghan Chen , Xin Li , Qiuling Song . Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates: A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives. Chinese Chemical Letters, 2024, 35(4): 108937-. doi: 10.1016/j.cclet.2023.108937
7. [7]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
8. [8]
  Yueying Yang , Huiru Xie , Xinbo Yu , Yang Liu , Hui Wang , Hua Li , Lixia Chen . Design, synthesis and evaluation of the first DYRK1A degrader for promoting the proliferation of pancreatic β-cells. Chinese Chemical Letters, 2024, 35(11): 109570-. doi: 10.1016/j.cclet.2024.109570
9. [9]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827
10. [10]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
11. [11]
  Gangsheng Li , Xiang Yuan , Fu Liu , Zhihua Liu , Xujie Wang , Yuanyuan Liu , Yanmin Chen , Tingting Wang , Yanan Yang , Peicheng Zhang . Three-step synthesis of flavanostilbenes with a 2-cyclohepten-1-one core by Cu-mediated [5 + 2] cycloaddition/decarboxylation cascade. Chinese Chemical Letters, 2025, 36(2): 109880-. doi: 10.1016/j.cclet.2024.109880
12. [12]
  Keke Han , Wenjun Rao , Xiuli You , Haina Zhang , Xing Ye , Zhenhong Wei , Hu Cai . Two new high-temperature molecular ferroelectrics [1,5-3.2.2-Hdabcni]X (X = ClO₄⁻, ReO₄⁻). Chinese Chemical Letters, 2024, 35(6): 108809-. doi: 10.1016/j.cclet.2023.108809
13. [13]
  Huimin Luan , Qinming Wu , Jianping Wu , Xiangju Meng , Feng-Shou Xiao . Templates for the synthesis of zeolites. Chinese Journal of Structural Chemistry, 2024, 43(4): 100252-100252. doi: 10.1016/j.cjsc.2024.100252
14. [14]
  Zhaojun Liu , Zerui Mu , Chuanbo Gao . Alloy nanocrystals: Synthesis paradigms and implications. Chinese Journal of Structural Chemistry, 2023, 42(11): 100156-100156. doi: 10.1016/j.cjsc.2023.100156
15. [15]
  Zhenhao Wang , Yuliang Tang , Ruyu Li , Shuai Tian , Yu Tang , Dehai Li . Bioinspired synthesis of cochlearol B and ganocin A. Chinese Chemical Letters, 2024, 35(7): 109247-. doi: 10.1016/j.cclet.2023.109247
16. [16]
  Hui Jin , Qin Cai , Peiwen Liu , Yan Chen , Derong Wang , Weiping Zhu , Yufang Xu , Xuhong Qian . Multistep continuous flow synthesis of Erlotinib. Chinese Chemical Letters, 2024, 35(4): 108721-. doi: 10.1016/j.cclet.2023.108721
17. [17]
  Caihong Mao , Yanfeng He , Xiaohan Wang , Yan Cai , Xiaobo Hu . Synthesis and molecular recognition characteristics of a tetrapodal benzene cage. Chinese Chemical Letters, 2024, 35(8): 109362-. doi: 10.1016/j.cclet.2023.109362
18. [18]
  Mei Peng , Wei-Min He . Photochemical synthesis and group transfer reactions of azoxy compounds. Chinese Chemical Letters, 2024, 35(8): 109899-. doi: 10.1016/j.cclet.2024.109899
19. [19]
  Liyong Ding , Zhenhua Pan , Qian Wang . 2D photocatalysts for hydrogen peroxide synthesis. Chinese Chemical Letters, 2024, 35(12): 110125-. doi: 10.1016/j.cclet.2024.110125
20. [20]
  Xiaoyu Chen , Jiahao Hu , Jingyi Lin , Haiyang Huang , Changqing Ye , Hongli Bao . Biisoindolylidene solvatochromic fluorophores: Synthesis and photophysical properties. Chinese Chemical Letters, 2025, 36(2): 109923-. doi: 10.1016/j.cclet.2024.109923

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(596)
HTML views(16)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142