Citation: Zhi-Wei Chen, Jun-Bo Hou, Zhao-Ran Dai, Xiao-Feng Yang. A regioselective synthesis of pentacyclic compounds containing coumarin, pyrrole, indene without catalysts under microwave irradiation[J]. Chinese Chemical Letters, ;2016, 27(10): 1622-1625. doi: 10.1016/j.cclet.2016.04.009 shu

A regioselective synthesis of pentacyclic compounds containing coumarin, pyrrole, indene without catalysts under microwave irradiation

Key Laboratory for Green Pharmaceutical Technologies and Related Equipment of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China

Corresponding author: Zhi-Wei Chen, chenzhiwei@zjut.edu.cn
Received Date: 2 March 2016
Revised Date: 25 March 2016
Accepted Date: 6 April 2016
Available Online: 22 October 2016

Figures(2)

A concise and efficient approach was developed for the synthesis of pentacyclic compounds containing coumarin, pyrrole, indene in a regioselective manner in good yields via the reactions of N-substituted 4-aminocoumarin compounds and ninhydrin using microwave irradiation. No catalysts are required in our protocol.
- 4-Aminocoumarin,
- Catalyst-free,
- Ninhydrin,
- Regioselective,
- Annulation
1. [1]
  (a) R.J. Anderson, D.J. Faulkner, C.H. Cun, et al., Metabolites of the marine prosobranch mollusk Lamellaria sp., J. Am. Chem. Soc. 107(1985) 5492-5495; (b) N.Lindquist, W. Fenical, G.D. Van Duyne, et al., New alkaloids of the lamellarin class from the marine ascidian Didemnum chartaceum, J. Org. Chem. 53(1988) 4570-4574; (c) H. Kang, W. Fenical, A.-D. Ningalins, Novel aromatic alkaloids from a western Australian ascidian of the genus Didemnum, J. Org. Chem. 62(1997) 3254-3262; (d) S. Stanchev, G. Momekov, F. Jensen, et al., Synthesis, computational study and cytotoxic activity of new 4-hydroxycoumarin derivatives, Eur. J. Med. Chem. 43(2008) 694-706;(e) S.Sardari,Y.Mori,K.Horita,etal.,Synthesisandantifungalactivityofcoumarins and angular furanocoumarins, Bioorg. Med. Chem. 7(1999) 1933-1940.
2. [2]
  (a) J. Ham, H. Kang, A novel cytotoxic alkaloid of lamellarin class from a marine ascidian Didemnum sp., Bull. Korean Chem. Soc. 23(2002) 163-166; (b) Z.H. Sui, J.H. Guan, M.J. Macielag, et al., Synthesis and biological activities of novel b-carbolines as PDE5 inhibitors, Bioorg. Med. Chem. 13(2003) 761-765; (c) S.A. Yamashkin, L.G. Yudin, A.N. Kost, Synthesis of pyrroloquinolones, Chem. Heterocycl. Compd. 19(1983) 401-405; (d) H. Fan, J.N. Peng, M.T. Hamann, et al., Lamellarins and related pyrrole-derived alkaloids from marine organisms, Chem. Rev. 108(2008) 264-287.
3. [3]
  D. Pla, A. Marchal, C.A. Olsen. Modular total synthesis of lamellarin D[J]. J. Org. Chem., 2005,70:8231-8234. doi: 10.1021/jo051083a
4. [4]
  (a) L. Perreux, A. Loupy, A tentative rationalization of microwave effects in organic synthesis according to the reaction medium and mechanistic considerations, Tetrahedron 57(2003) 9199-9223; (b) P. Lidstrom, J. Tierney, B. Wathey, et al., Microwave assisted organic synthesis-a review, Tetrahedron 57(2001) 9225-9283; (c) D. Bogdal, J. Pielichowski, A. Boron, New synthetic method of aromatic ethers under microwave irradiation in dry media, Synth. Commun. 28(1998) 3029; (d) J. Westman, An efficient combination of microwave dielectric heating and the use of solid-supported triphenylphosphine for Wittig reactions, Org. Lett. 3(2001) 3745-3747.
5. [5]
  (a) Z.W. Chen, Q. Zhu, W.K. Su, A novel sulfonic acid functionalized ionic liquid catalyzed multicomponent synthesis of 10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-dione derivatives in water, Tetrahedron Lett. 52(2011); (b) Z.W. Chen, J.H. Bi, W.K. Su, Synthesis and antitumor activity of novel coumarin derivatives via a three-component reaction in water, Chin. J. Chem. 31(2013) 507-514; (c) Z.W. Chen, X.F. Yang, W.K. Su, An efficient protocol for multicomponent synthesis of functionalized chromeno[4, 3-b]pyrrol-4(1H)-one derivatives, Tetrahedron Lett. 56(2015) 2476-2479.
6. [6]
  S.Y. Peng, L. Wang, J.Y. Huang. Palladium-catalyzed oxidative annulation via C-H/N-H functionalization:access to substituted pyrroles[J]. Adv. Synth. Catal., 2013,335:2550-2557.
7. [7]
  (a) D.W. Brown, P.R. Graupner, M. Sainsbury, et al., New antioxidants incorporating indole and indoline chromophores, Tetrahedron 47(1991) 4383-4408; (b) J.A. Butera, S.A. Antane, B. Hirth, et al., Synthesis and potassium channel opening activity of substituted 10H-benzo and furo[3,2-b]indole- and 5,10-dihydro-indeno[1,2-b]indole-1-carboxylic acids, Bioorg. Med. Chem. Lett. 11(2001) 2093-2097.
8. [8]
  (a) S. Hanessian, U. Reinhold, M. Saulnier, et al., Probing the importance of spacial and conformational domains in captopril analogs for angiotensin converting enzyme activity, Bioorg. Med. Chem. Lett. 8(1998) 2123-2128; (b) M.A. Ondetti, D.W. Cushman, Inhibition of the renin-angiotensin system. A new approach to the therapy of hypertension, J. Med. Chem. 24(1981) 355-361; (c) J.A. Robl, M.P. Cimarusti, L.M. Simpkins, et al., Peptidomimetic synthesis:a novel, highly stereoselective route to substituted freidinger lactams, J. Am. Chem. Soc. 116(1994) 2348-2355.
9. [9]
  S. Hayashibem, S. Yamasaki, N. Shiraishi, et al., Fused Indane Compound, WO 2009069610, 2009.
10. [10]
  K. Pradhan, S. Paul, A.R. Das. Synthesis of indeno and acenaphtho cores containing dihydroxy indolone, pyrrole, coumarin and uracil fused heterocyclic motifs under sustainable conditions exploring the catalytic role of the SnO2 quantum dot[J]. RSC Adv., 2015,5:12062-12070. doi: 10.1039/C4RA12618A
11. [11]
  S. Muthusaravanan, C. Sasikumar, B.D. Bala. An eco-friendly three-component regio- and stereoselective synthesis of highly functionalized dihydroindeno[1,2-b]pyrroles under grinding[J]. Green Chem., 2014,16:1297-1304. doi: 10.1039/C3GC42150C
12. [12]
  B. Jiang, Q.Y. Li, S.J. Tu. Three-component domino reactions for selective formation of indeno[1, 2-b]indole derivatives[J]. Org. Lett, 2012,14:5210-5213. doi: 10.1021/ol3023038
13. [13]
  A. Abdolali, Z. Ameneh, R. Atieh. A novel and one-pot multicomponent approach to the synthesis of dihyroindeno[1, 2-b]pyrroles and indeno[20,10:4,5]pyrrolo[1,2-a]-fused 1,3-diazaheterocycles[J]. Synthesis, 2011,3:497-501.
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