How to cite this paper
Zeidanlu, A., Sheikh, S., Lari, J & Vahedi, H. (2017). Synthesis of ethyl-3-amino-1-aryl-1H-benzo[f]chromeme-2-carboxylate derivatives promoted by DMAP.Current Chemistry Letters, 6(3), 117-124.
Refrences
1 Kang Y., Du Y., and Jin Z. (2003) Total synthesis of the highly potent anti-HIV natural product daurichromenic acid along with its two chromane derivatives. Org. Lett., 5 (23) 4481-4484.
2 Kidwai M., Saxena S., Rahman Khan M. K., and Thukral S. S. (2005) Aqua mediated synthesis of substituted 2-amino-4H-chromenes and in vitro study as antibacterial agents. Bioorg. Med. Chem. Lett., 15 (19) 4295-4298.
3 Lagisetti C., Pourpak A., Jiang Q., Cui X., Goronga T., Morris S. W., and Webb T. R. (2008) Antitumor compounds based on a natural product consensus pharmacophore. J. Med. Chem., 51 (19) 6220-6224 .
4 Bianchi G., and Tava A. (1987) Synthesis of (2R)-(+)2, 3-Dihydro-2, 6-dimethyl-4H-pyran-4-one, a homologue of pheromones of a species in the Hepialidae family. Agric. Biol. Chem., 51, 2001-2002.
5 Khafagy M. M., El-Wahab A. H. A., Eid F. A., and El-Agrody A. M. (2002) Synthesis of halogen derivatives of benzo [h] chromene and benzo [a] anthracene with promising antimicrobial activities. II Farmaco., 57 (9) 715-722.
6 Cheng J. F., Ishikawa A., Ono Y., Arrhenius T. and Nadzan A. (2003) Novel Chromene Derivatives as TNF-α Inhibitors. Bioorg. Med. Chem. Lett., 13 (21) 3647-3650.
7 Mun J., Jabbar A. A., Devi N. S., Liu Y., Van Meir E. G., and Goodman M. M. (2012) Structure–activity relationship of 2,2-dimethyl-2H-chromene based arylsulfonamide analogs of 3, 4-dimethoxy-N-[(2, 2-dimethyl-2H-chromen-6-yl) methyl]-N-phenylbenzenesulfonamid e, a novel small molecule hypoxia inducible factor-1(HIF-1) pathway inhibitor and anti-cancer agent., Bioorg. Med. Chem., 20 (14) 4590-4597.
8 Suresh T., Arunima V., Atin K., Sandeep G., Prarthana V. R. and Ganesh R. K. (2010) Novel chromeneimidazole derivatives as antifungal compounds: synthesis and in vitro evaluation. Acta Pol. Pharm., 67, 423-427.
9 Jain N., Xu J., Ramesh M., Du F., Jian-Zhong G., Emmanuel P., and Sui Z. (2009) Identification and Structure− Activity Relationships of Chromene-Derived Selective Estrogen Receptor Modulators for Treatment of Postmenopausal Symptoms. J. Med. Chem., 52 (23) 7544-7569.
10 Mart´ınez-Grau A., and Marco J. L. (1997) Friedlander reaction on 2-amino-3-cyano-4H-pyrans: synthesis of derivates of 4Hpyran[2,3-b]quinoline, new tacrine analogues. Bioorg. Med. Chem. Lett. 7 (24) 3165–3170.
11 Denish C. K., Hetal K. P., and Nilesh K. G. (2012) Synthesis, characterization and anti-HIV activity of 4-Hydroxy-3-(5-methylisoxazol-3-yl)pyrano(3,2-C)chromene-2,5-dione. Asian J. Biochem. Pharm. Res., 2 (2) 126-130.
12 (a) Ellis G. P. (1977) In The Chemistry of Heterocyclic of Compounds. Chromenes, Harmonesand Chromones; Weissberger, A., Taylor, E. C., Eds.; John Wiley: New York, NY,; Chapter II, pp 11e13; (b) Klocke J. A., Balandrin M. F., Adams R. P., and Kingsford E. (1985). Insecticidal chromenes from the volatile oil of Hemizonia fitchii. J. chem. eco., 11 (6) 701-712.
13 Gong K., Wang H. L., Fang D., and Liu Z. L. (2008) Basic ionic liquid as catalyst for the rapid and green synthesis of substituted 2-amino-2-chromenes in aqueous media. Catal. Commun., 9 (5) 650-653.
14 Sabitha G., Bhikshapathi M., Nayak S., Srinivas R., and Yadav J. S. (2011) Triton B Catalyzed Three‐Component, One‐Pot Synthesis of 2‐Amino‐2‐chromenes at Ambient Temperature. J. Heterocycl. Chem., 48 (2) 267-271.
15 Kidwai M., Saxena S., Khan M. K. R., and Thukral, S. S. (2005) Aqua mediated synthesis of substituted 2-amino-4H-chromenes and in vitro study as antibacterial agents. Bioorg. Med. Chem. Lett., 15 (19) 4295-4298.
16 Mirza-Aghayan M., Nazmdeh S., Boukherroub R., Rahimifard M., Tarlani A. A., and Abolghasemi-Malakshah M. (2013) Convenient and Efficient One-Pot Method for the Synthesis of 2-Amino-tetrahydro-4 H-chromenes and 2-Amino-4 H-benzo [h]-chromenes Using Catalytic Amount of Amino-Functionalized MCM-41 in Aqueous Media. Synth. Commun., 43 (11) 1499-1507.
17 Ballini R., Bosica G., Conforti M. L., Maggi R., Mazzacani A., Righi P., and Sartori G. (2001) Three-component process for the synthesis of 2-amino-2-chromenes in aqueous media. Tetrahedron., 57 (7) 1395-1398.
18 Jin T. S., Xiao J. C., Wang S. J., and Li T. S. (2004) Ultrasound-assisted synthesis of 2-amino-2-chromenes with cetyltrimethylammonium bromide in aqueous media. Ultra. Sonochem., 11 (6) 393-397.
19 Zhou Z., Yang F., Wu L., and Zhang A. (2012) Potassium phosphate tribasic trihydrate as catalyst for the rapid and clean one-pot synthesis of 2-amino-4H-chromenes under solvent-free conditions. Chem. Sci. Trans., 1 (1) 57-60.
20 Mobinikhaledi A., Moghanian H., and Sasani F. (2011). Microwave-assisted one-pot synthesis of 2-amino-2-chromenes using piperazine as a catalyst under solvent-free conditions. Synthesis and Reactivity in Inorganic. Inorg., Met. Org., Nano-Met. Chem., 41 (3) 262-265.
21 Kalla R. M. N., Byeon S. J., Heo M. S., and Kim I. (2013) Synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates and 2-amino-4H-chromenes catalyzed by tetramethylguanidine. Tetrahedron., 69 (49) 10544-10551.
22 Heravi M. M., Bakhtiari K., Zadsirjan V., Bamoharram F. F., and Heravi O. M. (2007) Aqua mediated synthesis of substituted 2-amino-4H-chromenes catalyzed by green and reusable Preyssler heteropolyacid. Bioorg. Med. Chem. Lett., 17 (15) 4262-4265.
23 Behbahani F. K., and Maryam S. (2013) On Water CuSO4. 5H2O-catalyzed Synthesis of 2-amino-4H-chromenes. J. Korean Chem. Soc., 57 (3) 357-360.
24 Heravi M. M., Baghernejad B. and Oskooie H. A. (2008) A novel and efficient catalyst to one-pot synthesis of 2-amino- 4H-chromenes by methanesulfonic acid. J. Chin. Biochem. Soc., 55 (3) 659-662.
25 Wang X. S., Shi D. Q., Yu H. Z., Wang G. F. and Tu S. (2004) Synthesis of 2-aminochromene derivatives catalyzed by KF/Al2O3. J. Synth. Commun., 34 (3) 509-514.
26 Dekamin M. G., Eslami M., and Maleki A. (2013) Potassium phthalimide-N-oxyl: a novel, efficient, and simple organocatalyst for the one-pot three-component synthesis of various 2-amino-4H-chromene derivatives in water. Tetrahedron., 69 (3) 1074-1085.
27 Solhy A., Elmakssoudi A., Tahir R., Karkouri M., Larzek M., Bousmina M., and Zahouily M. (2010) Clean chemical synthesis of 2-amino-chromenes in water catalyzed by nanostructured diphosphate Na2CaP2O7. Green Chem., 12 (12) 2261-2267.
28 Maleki B., and Sheikh S. (2015) Nano polypropylenimine dendrimer (DAB-PPI-G1): as a novel nano basic-polymer catalyst for one-pot synthesis of 2-amino-2-chromene derivatives. RSC Adv., 5 (54) 42997-43005.
29 Raghuvanshi D. S., and Singh K. N. (2010) An expeditious synthesis of novel pyranopyridine derivatives involving chromenes under controlled microwave irradiation. ARKIVOC., 10, 305-317
30 Maleki B, and Sheikh S. (2015) One-pot Synthesis of 2-Amino-2-chromene and 2-Amino-3-cyano-4H-pyran Derivatives promoted by Potassium Fluoride. Org. Prep. Proced. Int., 47 (5) 368-378.
31 Kolla S. R., and Lee Y. R. (2011) Ca(OH)2-mediated efficient synthesis of 2-amino-5-hydroxy-4H-chromene derivatives with various substituents. Tetrahedron., 67 (43) 8271-8275.
32 Tayebee R., Maleki B., Mohammadi Zonoz F., and Kakhi. Kunani R.M. (2016) Mild, efficient, and environmentally friendly synthesis of symmetrical N, N-alkylidenebisamides under solvent-free conditions catalyzed by H7[(P2W17O61)FeIII(H2O)]. RSC Adv., 6 (25) 20687-20694.
33 Maleki B., Babaee S., and Tayebee R. (2015) Zn (L-Proline)2: as a powerful and reusable organomettalic catalyst for the very fast synthesis of 2-amino-4H-benzo[g]chromene derivatives under solvent-free conditions, Appl. Organomet. Chem., 29, 408-411.
34 Maleki B., Rezaei Seresht E., and Ebrahimi Z. (2015) Friedlander Synthesis of Quinolines Promoted By Polymer-bound Sulfonic Acid. Org. Prep. Proced. Int., 47, 149-160.
35 Maleki B. (2015) Solvent-free Synthesis of 2,4,6-Triarylpyridine Derivatives Promoted by 1,3-Dibromo-5,5-dimethylhydantoin, Org. Prep. Proced. Int., 47, 173-178.
36 Rimaz M., Mousavi H., Keshavarz P., and Khalili, B. (2015) ZrOCl2. 8H2O as a green and efficient catalyst for the expeditious synthesis of substituted 3-arylpyrimido [4, 5-c] pyridazines in water. Curr. Chem. Lett., 4 (4) 159-168.
37 Zonouz A., Eskandari I., and Notash, B. (2015) An efficient and green procedure for the synthesis of highly substituted polyhydronaphthalene derivatives via a one-pot, multi-component reaction in aqueous media. Curr. Chem. Lett., 4 (3) 85-92.
38 Sarrafi Y., Pazokie F., Azizi S., Alimohammadi K., Mehrasbi E., and Chiani E., (2014) Mesoporous SBA-15 nanoparticles: An efficient and eco-friendly Catalyst for one-pot synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones under solvent-free conditions. Curr. Chem. Lett., 3 (2) 97-102.
2 Kidwai M., Saxena S., Rahman Khan M. K., and Thukral S. S. (2005) Aqua mediated synthesis of substituted 2-amino-4H-chromenes and in vitro study as antibacterial agents. Bioorg. Med. Chem. Lett., 15 (19) 4295-4298.
3 Lagisetti C., Pourpak A., Jiang Q., Cui X., Goronga T., Morris S. W., and Webb T. R. (2008) Antitumor compounds based on a natural product consensus pharmacophore. J. Med. Chem., 51 (19) 6220-6224 .
4 Bianchi G., and Tava A. (1987) Synthesis of (2R)-(+)2, 3-Dihydro-2, 6-dimethyl-4H-pyran-4-one, a homologue of pheromones of a species in the Hepialidae family. Agric. Biol. Chem., 51, 2001-2002.
5 Khafagy M. M., El-Wahab A. H. A., Eid F. A., and El-Agrody A. M. (2002) Synthesis of halogen derivatives of benzo [h] chromene and benzo [a] anthracene with promising antimicrobial activities. II Farmaco., 57 (9) 715-722.
6 Cheng J. F., Ishikawa A., Ono Y., Arrhenius T. and Nadzan A. (2003) Novel Chromene Derivatives as TNF-α Inhibitors. Bioorg. Med. Chem. Lett., 13 (21) 3647-3650.
7 Mun J., Jabbar A. A., Devi N. S., Liu Y., Van Meir E. G., and Goodman M. M. (2012) Structure–activity relationship of 2,2-dimethyl-2H-chromene based arylsulfonamide analogs of 3, 4-dimethoxy-N-[(2, 2-dimethyl-2H-chromen-6-yl) methyl]-N-phenylbenzenesulfonamid e, a novel small molecule hypoxia inducible factor-1(HIF-1) pathway inhibitor and anti-cancer agent., Bioorg. Med. Chem., 20 (14) 4590-4597.
8 Suresh T., Arunima V., Atin K., Sandeep G., Prarthana V. R. and Ganesh R. K. (2010) Novel chromeneimidazole derivatives as antifungal compounds: synthesis and in vitro evaluation. Acta Pol. Pharm., 67, 423-427.
9 Jain N., Xu J., Ramesh M., Du F., Jian-Zhong G., Emmanuel P., and Sui Z. (2009) Identification and Structure− Activity Relationships of Chromene-Derived Selective Estrogen Receptor Modulators for Treatment of Postmenopausal Symptoms. J. Med. Chem., 52 (23) 7544-7569.
10 Mart´ınez-Grau A., and Marco J. L. (1997) Friedlander reaction on 2-amino-3-cyano-4H-pyrans: synthesis of derivates of 4Hpyran[2,3-b]quinoline, new tacrine analogues. Bioorg. Med. Chem. Lett. 7 (24) 3165–3170.
11 Denish C. K., Hetal K. P., and Nilesh K. G. (2012) Synthesis, characterization and anti-HIV activity of 4-Hydroxy-3-(5-methylisoxazol-3-yl)pyrano(3,2-C)chromene-2,5-dione. Asian J. Biochem. Pharm. Res., 2 (2) 126-130.
12 (a) Ellis G. P. (1977) In The Chemistry of Heterocyclic of Compounds. Chromenes, Harmonesand Chromones; Weissberger, A., Taylor, E. C., Eds.; John Wiley: New York, NY,; Chapter II, pp 11e13; (b) Klocke J. A., Balandrin M. F., Adams R. P., and Kingsford E. (1985). Insecticidal chromenes from the volatile oil of Hemizonia fitchii. J. chem. eco., 11 (6) 701-712.
13 Gong K., Wang H. L., Fang D., and Liu Z. L. (2008) Basic ionic liquid as catalyst for the rapid and green synthesis of substituted 2-amino-2-chromenes in aqueous media. Catal. Commun., 9 (5) 650-653.
14 Sabitha G., Bhikshapathi M., Nayak S., Srinivas R., and Yadav J. S. (2011) Triton B Catalyzed Three‐Component, One‐Pot Synthesis of 2‐Amino‐2‐chromenes at Ambient Temperature. J. Heterocycl. Chem., 48 (2) 267-271.
15 Kidwai M., Saxena S., Khan M. K. R., and Thukral, S. S. (2005) Aqua mediated synthesis of substituted 2-amino-4H-chromenes and in vitro study as antibacterial agents. Bioorg. Med. Chem. Lett., 15 (19) 4295-4298.
16 Mirza-Aghayan M., Nazmdeh S., Boukherroub R., Rahimifard M., Tarlani A. A., and Abolghasemi-Malakshah M. (2013) Convenient and Efficient One-Pot Method for the Synthesis of 2-Amino-tetrahydro-4 H-chromenes and 2-Amino-4 H-benzo [h]-chromenes Using Catalytic Amount of Amino-Functionalized MCM-41 in Aqueous Media. Synth. Commun., 43 (11) 1499-1507.
17 Ballini R., Bosica G., Conforti M. L., Maggi R., Mazzacani A., Righi P., and Sartori G. (2001) Three-component process for the synthesis of 2-amino-2-chromenes in aqueous media. Tetrahedron., 57 (7) 1395-1398.
18 Jin T. S., Xiao J. C., Wang S. J., and Li T. S. (2004) Ultrasound-assisted synthesis of 2-amino-2-chromenes with cetyltrimethylammonium bromide in aqueous media. Ultra. Sonochem., 11 (6) 393-397.
19 Zhou Z., Yang F., Wu L., and Zhang A. (2012) Potassium phosphate tribasic trihydrate as catalyst for the rapid and clean one-pot synthesis of 2-amino-4H-chromenes under solvent-free conditions. Chem. Sci. Trans., 1 (1) 57-60.
20 Mobinikhaledi A., Moghanian H., and Sasani F. (2011). Microwave-assisted one-pot synthesis of 2-amino-2-chromenes using piperazine as a catalyst under solvent-free conditions. Synthesis and Reactivity in Inorganic. Inorg., Met. Org., Nano-Met. Chem., 41 (3) 262-265.
21 Kalla R. M. N., Byeon S. J., Heo M. S., and Kim I. (2013) Synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates and 2-amino-4H-chromenes catalyzed by tetramethylguanidine. Tetrahedron., 69 (49) 10544-10551.
22 Heravi M. M., Bakhtiari K., Zadsirjan V., Bamoharram F. F., and Heravi O. M. (2007) Aqua mediated synthesis of substituted 2-amino-4H-chromenes catalyzed by green and reusable Preyssler heteropolyacid. Bioorg. Med. Chem. Lett., 17 (15) 4262-4265.
23 Behbahani F. K., and Maryam S. (2013) On Water CuSO4. 5H2O-catalyzed Synthesis of 2-amino-4H-chromenes. J. Korean Chem. Soc., 57 (3) 357-360.
24 Heravi M. M., Baghernejad B. and Oskooie H. A. (2008) A novel and efficient catalyst to one-pot synthesis of 2-amino- 4H-chromenes by methanesulfonic acid. J. Chin. Biochem. Soc., 55 (3) 659-662.
25 Wang X. S., Shi D. Q., Yu H. Z., Wang G. F. and Tu S. (2004) Synthesis of 2-aminochromene derivatives catalyzed by KF/Al2O3. J. Synth. Commun., 34 (3) 509-514.
26 Dekamin M. G., Eslami M., and Maleki A. (2013) Potassium phthalimide-N-oxyl: a novel, efficient, and simple organocatalyst for the one-pot three-component synthesis of various 2-amino-4H-chromene derivatives in water. Tetrahedron., 69 (3) 1074-1085.
27 Solhy A., Elmakssoudi A., Tahir R., Karkouri M., Larzek M., Bousmina M., and Zahouily M. (2010) Clean chemical synthesis of 2-amino-chromenes in water catalyzed by nanostructured diphosphate Na2CaP2O7. Green Chem., 12 (12) 2261-2267.
28 Maleki B., and Sheikh S. (2015) Nano polypropylenimine dendrimer (DAB-PPI-G1): as a novel nano basic-polymer catalyst for one-pot synthesis of 2-amino-2-chromene derivatives. RSC Adv., 5 (54) 42997-43005.
29 Raghuvanshi D. S., and Singh K. N. (2010) An expeditious synthesis of novel pyranopyridine derivatives involving chromenes under controlled microwave irradiation. ARKIVOC., 10, 305-317
30 Maleki B, and Sheikh S. (2015) One-pot Synthesis of 2-Amino-2-chromene and 2-Amino-3-cyano-4H-pyran Derivatives promoted by Potassium Fluoride. Org. Prep. Proced. Int., 47 (5) 368-378.
31 Kolla S. R., and Lee Y. R. (2011) Ca(OH)2-mediated efficient synthesis of 2-amino-5-hydroxy-4H-chromene derivatives with various substituents. Tetrahedron., 67 (43) 8271-8275.
32 Tayebee R., Maleki B., Mohammadi Zonoz F., and Kakhi. Kunani R.M. (2016) Mild, efficient, and environmentally friendly synthesis of symmetrical N, N-alkylidenebisamides under solvent-free conditions catalyzed by H7[(P2W17O61)FeIII(H2O)]. RSC Adv., 6 (25) 20687-20694.
33 Maleki B., Babaee S., and Tayebee R. (2015) Zn (L-Proline)2: as a powerful and reusable organomettalic catalyst for the very fast synthesis of 2-amino-4H-benzo[g]chromene derivatives under solvent-free conditions, Appl. Organomet. Chem., 29, 408-411.
34 Maleki B., Rezaei Seresht E., and Ebrahimi Z. (2015) Friedlander Synthesis of Quinolines Promoted By Polymer-bound Sulfonic Acid. Org. Prep. Proced. Int., 47, 149-160.
35 Maleki B. (2015) Solvent-free Synthesis of 2,4,6-Triarylpyridine Derivatives Promoted by 1,3-Dibromo-5,5-dimethylhydantoin, Org. Prep. Proced. Int., 47, 173-178.
36 Rimaz M., Mousavi H., Keshavarz P., and Khalili, B. (2015) ZrOCl2. 8H2O as a green and efficient catalyst for the expeditious synthesis of substituted 3-arylpyrimido [4, 5-c] pyridazines in water. Curr. Chem. Lett., 4 (4) 159-168.
37 Zonouz A., Eskandari I., and Notash, B. (2015) An efficient and green procedure for the synthesis of highly substituted polyhydronaphthalene derivatives via a one-pot, multi-component reaction in aqueous media. Curr. Chem. Lett., 4 (3) 85-92.
38 Sarrafi Y., Pazokie F., Azizi S., Alimohammadi K., Mehrasbi E., and Chiani E., (2014) Mesoporous SBA-15 nanoparticles: An efficient and eco-friendly Catalyst for one-pot synthesis of 3, 4-dihydropyrimidin-2 (1H)-ones under solvent-free conditions. Curr. Chem. Lett., 3 (2) 97-102.