One-Pot Synthesis of Pyranocarbazoles by Ethylenediamine Diacetate Catalyzed Domino Aldol-Type Reaction/6π-Electrocyclization of Hydroxycarbazoles to α,β-Unsaturated Aldehydes and Conversion into Other Pyranocarbazoles

Rameshwar Prasad Pandit; Yong Rok Lee

doi:10.1055/s-0032-1316766

Synthesis, Table of Contents

Synthesis 2012; 44(18): 2910-2918
DOI: 10.1055/s-0032-1316766

paper

One-Pot Synthesis of Pyranocarbazoles by Ethylenediamine Diacetate Catalyzed Domino Aldol-Type Reaction/6π-Electrocyclization of Hydroxycarbazoles to α,β-Unsaturated Aldehydes and Conversion into Other Pyranocarbazoles

Rameshwar Prasad Pandit

School of Chemical Engineering, Yeungnam University, Gyeongsan 712-749, Korea, Fax: +82(53)8104631 Email: yrlee@yu.ac.kr

,

Yong Rok Lee*

School of Chemical Engineering, Yeungnam University, Gyeongsan 712-749, Korea, Fax: +82(53)8104631 Email: yrlee@yu.ac.kr

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Abstract

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Abstract

A new synthetic route for biologically interesting pyranocarbazoles was developed by reaction of 2- or 4-hydroxycarbazole with α,β-unsaturated aldehydes in the presence of ethylenediamine diacetate (EDDA). The key strategy of this methodology is a formal [3+3] cycloaddition via domino aldol-type/6π-electrocyclization. The synthesized pyranocarbazoles can be converted into derivatives bearing substituents on the carbazole and pyran rings.

Key words

pyranocarbazoles - ethylenediamine diacetate - domino reaction - heterocycles - cyclization

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References

References

1a Knölker H.-J, Reddy KR In The Alkaloids . Vol. 65. Cordell GA. Academic Press; Amsterdam: 2008: 1-430
1b Cuong NM, Hung TQ, Van Sung T. Chem. Pharm. Bull. 2004; 52: 1175
1c Pacher T, Bacher M, Hofer O, Greger H. Phytochemistry 2001; 58: 129
1d Knölker H.-J. Curr. Org. Synth. 2004; 1: 309

2a Knölker H.-J, Reddy KR. Chem. Rev. 2002; 102: 4303
2b Forke R, Gruner KK, Knott KE, Auschill S, Agarwal S, Martin R, Böhl M, Richter S, Tsiavaliaris G, Fedorov R, Manstein DJ, Gutzeit HO, Knölker H.-J. Pure Appl. Chem. 2010; 82: 1975

3a Chakraborty DP, Das KC, Chowdhury BK. J. Org. Chem. 1971; 36: 725
3b Joshi BS, Kamat VN, Gawad DH. Tetrahedron 1970; 26: 1475
3c Tachibana T, Kikuzaki H, Lajis NH, Nakatani N. J. Agric. Food Chem. 2003; 51: 6461

4 Tachibana Y, Kikuzaki H, Lajis NH, Nakatani N. J. Agric. Food Chem. 2001; 49: 5589
5 Chevallier A. The Encyclopedia of Medicinal Plants . Dorling Kindersley; London: 1996
6 Cui C.-B, Yan S.-Y, Cai B, Yao X.-S. J. Asian Nat. Prod. Res. 2002; 4: 233
7 Ruangrungsi N, Ariyaprayoon J, Lange GI, Organ MG. J. Nat. Prod. 1990; 53: 946
8 Gruner KK, Hopfmann T, Matsumoto K, Jager A, Katsuki T, Knolker H.-J. Org. Biomol. Chem. 2011; 9: 2057
9 Furukawa H, Wu T.-S, Kuoh C.-S. Heterocycles 1985; 23: 1391
10 Birari R, Javia V, Bhutani KK. Fitoterapia 2010; 81: 1129
11 Dineshkumar B, Mitra A, Mahadevappa M. Int. J. Phytomed. 2010; 2: 22
12 Adebajo AC, Ayoola OF, Iwalewa EO, Akindahunsi AA, Omisore NO. A, Adewunmi CO. Adenowo T. K. Phytomedicine 2006; 13: 246
13 Rao LJ. M, Ramalakshmi K, Borse BB, Raghavan B. Food Chem. 2007; 100: 742
14 Nagappan T, Ramasamy P, Wahid ME. A, Segaran TC, Vairappan CS. Molecules 2011; 16: 9651
15 Kumar NS, Mukherjee PK, Bhadra S, Saha BP, Pal BC. Phytother. Res. 2010; 24: 629
16 Wu T.-S, Chan Y.-Y, Liou M.-J, Lin F.-W, Shi L.-S, Chen K.-T. Phytother. Res. 1998; 12: S80
17 Yamuna E, Prabakaran K, Zeller M, Rajendra Prasad KJ. Synth. Commun. 2012; 42: 1330
18 Prabakaran K, Zeller M, Prasad KJ. R. Synlett 2011; 1835
19 Sridharan M, Prasad KJ. R. Z. Naturforsch., B. 2008; 63: 1112

20a Lee YR, Choi JH, Yoon SH. Tetrahedron Lett. 2005; 46: 7539
20b Lee YR, Lee WK, Noh SK, Lyoo WS. Synthesis 2006; 853
20c Lee YR, Kim DH. Synthesis 2006; 603
20d Lee YR, Kim JH. Synlett 2007; 2232
20e Wang X, Lee YR. Synthesis 2007; 3044
20f Lee YR, Xia L. Synthesis 2007; 3240
20g Lee YR, Kim YM. Helv. Chim. Acta 2007; 90: 2401
20h Lee YR, Li X, Kim JH. J. Org. Chem. 2008; 73: 4313
20i Xia L, Lee YR. Synlett 2008; 1643
20j Lee YR, Hung TV. Tetrahedron 2008; 64: 7338
20k Lee YR, Xia L. Tetrahedron Lett. 2008; 49: 3283
20l Lee YR, Kim YM, Kim SH. Tetrahedron 2009; 65: 101
20m Jung DH, Lee YR, Kim SH. Helv. Chim. Acta 2010; 93: 635

21 Saimoto H, Yoshida K, Murakami T, Morimoto M, Sashiwa H, Shigemasa Y. J. Org. Chem. 1996; 61: 6768
22 Kane VV, Martin AR, Peters JA. Heterocycles 1981; 16: 1445
23 Huang X, He Y, Chen Z, Hu C. Chin. J. Chem. 2009; 27: 1526

24a Parker KA, Mindt TL. Tetrahedron 2011; 69: 9779
24b Hsung RP, Shen HC, Douglas CJ, Morgan CD, Degen SJ, Yao LJ. J. Org. Chem. 1999; 64: 690
24c Shishido K, Hiroya K, Fukumoto K, Kametani T. Tetrahedron Lett. 1986; 27: 971

25a Wang X, Lee YR. Tetrahedron Lett. 2007; 48: 6275
25b Mudiganti NV. S, Claessens S, Habonimana P, De Kimpe N. J. Org. Chem. 2008; 73: 3867

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