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Tin(II)chloride catalyzed synthesis of pyranoquinolines, phenanthridinone and phenanthridine derivatives
Lingaiah Nagarapu (1,*)
, Rajashaker Bantu (2) , Ravinder Goud Puligoundla (3) (1) Organic Chemistry Division-II, Indian Institute of Chemical Technology, Hyderabad-500607, India
(2) Organic Chemistry Division-II, Indian Institute of Chemical Technology, Hyderabad-500607, India
(3) Organic Chemistry Division-II, Indian Institute of Chemical Technology, Hyderabad-500607, India
(*) Corresponding Author
Received: 27 Aug 2010 | Accepted: 30 Oct 2010 | Published: 30 Jun 2011 | Issue Date: June 2011
Abstract
A simple, efficient and cost-effective method for the synthesis of tetrahydropyranoquinoline derivatives by a one-pot condensation of aromatic aldehyde, aromatic amine and 3,4-dihydro-2H-pyran respectively in the presence of tin(II)chloride (SnCl2.2H2O) has been described.
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European Journal of Chemistry
Keywords
Synthesis; Tetrahydropyranoquinolines; 3,4-Dihydro-2H-pyran; Tin(II)chloride; Phenanthridine; Phenanthridinone
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DOI: 10.5155/eurjchem.2.2.260-265.263
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Citations
[1]. Atsushi Tochigi, Kadzuoki Tsukamoto, Noriyuki Suzuki, Yoshiro Masuyama
Catalytic Availabilities of Lewis Acidic SnCl2: Ph3PAuCl-SnCl2Composite Catalyzed Successiveortho-Alkenylation/O-Alkenylation of Phenols Followed by Cyclization to 1-Benzopyrans
European Journal of Organic Chemistry 2016(34), 5678, 2016
DOI: 10.1002/ejoc.201601042
[2]. Ravinder Goud Puligoundla, Hanmanth Reddy Vulupala, Nagaiah Kommu, Sudhakar Babu Kondra
Ceric Ammonium Nitrate (CAN)–Catalyzed, Efficient, One-Pot, Three-Component, aza-Diels–Alder Reactions for a Facile Synthesis of Tetrahydropyranoquinoline Derivatives
Synthetic Communications 45(4), 494, 2015
DOI: 10.1080/00397911.2014.956366
[3]. Víctor L. Rechac, Francisco G. Cirujano, Avelino Corma, Francesc X. Llabrés i Xamena
Diastereoselective Synthesis of Pyranoquinolines on Zirconium‐Containing UiO‐66 Metal‐Organic Frameworks
European Journal of Inorganic Chemistry 2016(27), 4512, 2016
DOI: 10.1002/ejic.201600372
[4]. Yoshiro Masuyama, Miki Hayashi, Noriyuki Suzuki
SnCl2-Catalyzed Propargylic Substitution of Propargylic Alcohols with Carbon and Nitrogen Nucleophiles
European Journal of Organic Chemistry 2013(14), 2914, 2013
DOI: 10.1002/ejoc.201201673
[5]. Khin Myat Noe Win, Amol D. Sonawane, Masayuki Ninomiya, Mamoru Koketsu
Iron(III) chloride and dialkyl diselenides promoted intramolecular cascade cyclization leading to synthesis of selenophene-fused quinoline based heterocycles
Tetrahedron Letters 101, 153907, 2022
DOI: 10.1016/j.tetlet.2022.153907
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[27]. Nagarapu, L.; Chary, M. V.; Satyender, A.; Srinivas, K. Cat. Communs. 2007, 8, 1173-1177.
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[28]. Nagarapu, L.; Rajashaker, B.; Rakesh, P. Appl. Catal. A: General 2007, 332, 304-309.
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[29]. Nagarapu, L.; Rajashaker, B.; Hari Babu, M. J. Heterocyclic Chem. 2009, 48(4), 728-731.
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[30]. Nagarapu, L.; Venkata Narsimhaji, C. H.; Shukla, C. K.; Rajashaker, B. Synthesis 2010, 3374-3378.
doi:10.1055/s-0030-1257973
[31]. Wildman, W. C. Alkaloids 1960, 6, 289-289.
[32]. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656-657.
doi:10.1070/RC1967v036n09ABEH001680
[33]. Yadav, J. S.; Subba Reddy, B. V.; Srinivas, R.; Kiran, K. S.; Kunwar, A. C. Tetrahedron 2003, 58, 1599-1604.
doi:10.1016/S0040-4020(03)00027-9
[2]. Yamada, N.; Kadowaki, S.; Takahashi, K.; Umezu, K. Biochem. Pharmacol. 1992, 44, 1211-1213.
doi:10.1016/0006-2952(92)90387-X
[3]. Faber, K.; Stueckler, H.; Kappe, T. J. Hetrocycl. Chem. 1984, 21, 1177-1181.
doi:10.1002/jhet.5570210450
[4]. Akhmed, Kh. S.; Bessonova, I. A. Dokl. Akad, Nauk. Uzh., SSR 1982, 34-36 (Russ.); Chem. Abstr. 1983, 98, 83727q.
[5]. Anzino, M.; Cappelli, A.; Vomero, S.; Cagnatto, A.; Skorupska, M. Med. Chem. Res. 1993, 3, 44-46.
[6]. Quraishi, M. A.; Thakur, V. R.; Dhawan, S. N. Indian J. Chem. Sect. B. 1989, 28B, 891-893.
[7]. Ramesh, M.; Mohan, P. S.; Shanmugam, P. Tetrahedron 1984, 40, 4041-4049.
doi:10.1016/0040-4020(84)85084-X
[8]. Young, K. K.; Sun, M. K.; Dae, Y. K. J. Am. Chem. Soc. 2010, 132, 1184-1149.
doi:10.1021/ja909713a
PMid:20050655
[9]. Vladimir, V. K. Tetrahedron 2009, 65, 2721-2750.
doi:10.1016/j.tet.2008.12.059
[10]. Paul, B.; Jonh-Carl, O.; Taeboem, O. Tetrahedron 2001, 57, 6099-6138.
doi:10.1016/S0040-4020(01)00438-0
[11]. Kametani, T.; Takeda, H.; Suzuki, Y.; Honda, T. Synth. Commun. 1985, 15, 499-505.
doi:10.1080/00397918508063833
[12]. Ma, Y.; Qian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462-6467.
doi:10.1021/jo982220p
[13]. Babu, G.; Perumal, P. T. Tetrahedron Lett. 1998, 39, 3225-3228.
doi:10.1016/S0040-4039(98)00397-9
[14]. Yadav, J. S.; Subba Reddy, B. V.; Srinivas. R.; Madhuri, Ch.; Ramalingam, T. Synlett. 2001, 0240-0242.
[15]. Mahesh, M.; Venkateswar, R. C.; Srinivas, R. K.; Raju, P. V. K.; Narayana, R. V. V. Synth. Commun. 2004, 34, 4089-4104.
doi:10.1081/SCC-200036586
[16]. Shivaji. V. M.; Sastry. M. N.; Ching-Fa, Y. Synlett. 2006, 1399-1403.
[17]. Min, X.; Yue-dong, L. Synlett. 2005, 2357-2361.
[18]. Gourhari, M.; Pradip, K. Tetrahedron Lett. 2006, 47, 5733-5736.
doi:10.1016/j.tetlet.2006.06.034
[19]. Mahajan, D.; Ganai, B. A.; Sharma, R. L.; Kapoor, K. K. Tetrahedron Lett. 2006, 47, 7919-7921.
doi:10.1016/j.tetlet.2006.09.007
[20]. Nagaiah, K.; Sreenu, D.; Rao, R. S.; Vashishta, G.; Yadav, J. S. Tetrahedron Lett. 2006, 47, 4409-4413.
doi:10.1016/j.tetlet.2006.04.085
[21]. Xing, X.; Wu, J.; Baishya, G.; Wei-Min, D. Tetrahedron 2006, 62, 11200-11206.
doi:10.1016/j.tet.2006.09.012
[22]. Gu, D. A.; Ji, S. H.; Jang, Z.Q.; Zhou, M. F.; Loh, T. P. Synlett. 2005, 0959-0962.
[23]. Yadav, J. S.; Subba Reddy, B.V.; Baishya, G.; Reddy, Narsaiah, K.V. Tetrahedron 2005, 61, 9541-9544.
doi:10.1016/j.tet.2005.07.095
[24]. Wang, B. Y.; Gu, C.; Luo, T.; Yang, L.; Suo, J. Tetrahedron Lett. 2004, 45, 3417-3419.
doi:10.1016/j.tetlet.2004.03.012
[25]. Rebeiro, G. L.; Khadlikar, B. M. Synthesis 2001, 0370-0372.
[26]. Nagarapu, L.; Venkateswarlu, P.; Gopal, P.; Srinivas, K.; Ruparani, P.; Radhika K. J. Mol. Cat. A: Chem. 2007, 26, 53-56.
doi:10.1016/j.molcata.2006.11.005
[27]. Nagarapu, L.; Chary, M. V.; Satyender, A.; Srinivas, K. Cat. Communs. 2007, 8, 1173-1177.
doi:10.1016/j.catcom.2006.11.003
[28]. Nagarapu, L.; Rajashaker, B.; Rakesh, P. Appl. Catal. A: General 2007, 332, 304-309.
doi:10.1016/j.apcata.2007.08.033
[29]. Nagarapu, L.; Rajashaker, B.; Hari Babu, M. J. Heterocyclic Chem. 2009, 48(4), 728-731.
doi:10.1002/jhet.135
[30]. Nagarapu, L.; Venkata Narsimhaji, C. H.; Shukla, C. K.; Rajashaker, B. Synthesis 2010, 3374-3378.
doi:10.1055/s-0030-1257973
[31]. Wildman, W. C. Alkaloids 1960, 6, 289-289.
[32]. Povarov, L. S. Russ. Chem. Rev. 1967, 36, 656-657.
doi:10.1070/RC1967v036n09ABEH001680
[33]. Yadav, J. S.; Subba Reddy, B. V.; Srinivas, R.; Kiran, K. S.; Kunwar, A. C. Tetrahedron 2003, 58, 1599-1604.
doi:10.1016/S0040-4020(03)00027-9
How to cite
Nagarapu, L.; Bantu, R.; Puligoundla, R.
Eur. J. Chem.
2011,
2(2), 260-265.
doi:10.5155/eurjchem.2.2.260-265.263
Nagarapu, L.; Bantu, R.; Puligoundla, R. Tin(II)chloride catalyzed synthesis of pyranoquinolines, phenanthridinone and phenanthridine derivatives.
Eur. J. Chem.
2011,
2(2), 260-265.
doi:10.5155/eurjchem.2.2.260-265.263
Nagarapu, L., Bantu, R., & Puligoundla, R.
(2011).
Tin(II)chloride catalyzed synthesis of pyranoquinolines, phenanthridinone and phenanthridine derivatives.
European Journal of Chemistry, 2(2), 260-265.
doi:10.5155/eurjchem.2.2.260-265.263
Nagarapu, Lingaiah, Rajashaker Bantu, & Ravinder Goud Puligoundla.
"Tin(II)chloride catalyzed synthesis of pyranoquinolines, phenanthridinone and phenanthridine derivatives." European Journal of Chemistry [Online], 2.2 (2011): 260-265. Web. 4 Jun. 2023
Nagarapu, Lingaiah, Bantu, Rajashaker, AND Puligoundla, Ravinder.
"Tin(II)chloride catalyzed synthesis of pyranoquinolines, phenanthridinone and phenanthridine derivatives" European Journal of Chemistry [Online], Volume 2 Number 2 (30 June 2011)
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.2.2.260-265.263
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