One-pot synthesis of substituted 4H-chromenes by three-component reaction of alkyl isocyanides, dialkyl acetylenedicarboxylates, and N-aryl-3- hydroxynaphthalene-2-carboxamide

Synthetic Communications

Volumn 41, Issue 24, 2011, Pages 3714-3719

  Hassanabadi, Alireza ^a   Mosslemin, Mohammad H ^b   Anary Abbasinejad, Mohammad ^b   Ghasemi, Maryam ^b  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

^b ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Acetylenic esters; Alkyl isocyanides; Multicomponent reactions; N aryl 3 hydroxynaphthalene 2 carboxamide; Substituted 4H chromenes

Indexed keywords

ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; ALKYL GROUP; ALKYLISOCYANIDE DERIVATIVE; AMIDE; CHROMENE DERIVATIVE; DIALKYLACETYLENEDICARBOXYLATE DERIVATIVE; DIETHYL 3 CYCLOHEXYLAMINO 5 O TOLYLCARBAMOYL 1H BENZO[F]CHROMENE 1,2 DICARBOXYLATE DERIVATIVE; DIMETHYL 3 CYCLOHEXYLAMINO 5 PHENYLCARBAMOYL 1H BENZO[F]CHROMENE 1,2 DICARBOXYLATE DERIVATIVE; DIMETHYL 3 T BUTYLAMINO 5 O TOLYLCARBAMOYL 1H BENZO[F]CHROMENE 1,2 DICARBOXYLATE DERIVATIVE; DIMETHYL 3 T BUTYLAMINO 5 PHENYLCARBAMOYL 1H BENZO[F]CHROMENE 1,2 DICARBOXYLATE DERIVATIVE; DIT BUTYL 3 CYCLOHEXYLAMINO 5 PHENYLCARBAMOYL 1H BENZO[F]CHROMENE 1,2 DICARBOXYLATE DERIVATIVE; N ARYL 3 HYDROXYNAPHTHALENE 2 CARBOXAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ONE POT SYNTHESIS;

EID: 80052050628     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.520184     Document Type: Article

References (24)

1. Polyakov, V. V. Chemical modification of the natural flavonoid myricetin. Chem. Nat. Compd. 1999, 1, 21.
2. Harbone, J. B. (Ed.). The Flavonoids-Advances in Research; Chapman & Hall: London, 1988.
3. Ugi, I. Isonitrile Chemistry; Academic Press: London, 1971.
4. Ugi, I. From isocyanides via four-component condensations to antibiotic syntheses. Angew. Chem. Int. Ed. 1982, 21, 810.
5. Domling, A.; Ugi, I. Multicomponent reactions with isocyanides. Angew. Chem. Int. Ed. 2000, 39, 3168.
6. Walborsky, H. M.; Periasamy, M. P.; Patai, S.; Rappoport, Z. (Eds.). The Chemistry of Functional Groups Supplement C; Wiley: New York, 1983; chap. 20, p. 835.
7. Marcaccini, S.; Torroba, T. Use of isocyanides in heterocyclic synthesis. Org. Prep. Proc. Int. 1993, 25, 141.
8. Nair, V.; Vinod, A. U.; Menon, N. R. S.; Santhi, V.; Varma, R. L.; Viji, S.; Mathew, S.; Srinivas, R. Multicomponent reactions involving zwitterionic intermediates for the construction of heterocyclic systems: One-pot synthesis of aminofurans and iminolactones. Tetrahedron 2003, 59, 10279.
9. Oakes, T. R.; Donovan, D. J. Reactions of isocyanides with activated acetylenes in protic solvents. J. Org. Chem. 1973, 38, 1319.
10. Yavari, I.; Anary-Abbasinejad, M.; Alizadeh, A.; Hossaini, Z. A simple and efficient approach to the synthesis of highly functionalized fused benzochromenes. Tetrahedron 2003, 59, 1289.
11. Yavari, I.; Djahaniani, H.; Nasiri, F. Reaction between alkyl isocyanides and dimethyl acetylenedicarboxylate in the presence of polyhydroxybenzenes: Synthesis of 4H-chromene derivatives. Tetrahedron 2003, 59, 9409.
12. Kazemizadeh, A. R.; Ramazani, A. Three-component reaction of indane-1,2,3-trione, tosylmethyl isocyanide, and benzoic acid derivatives. Arkivoc 2008, 159.
13. Kazemizadeh, A. R.; Ramazani, A. Passerini multicomponent reaction of indane-1,2,3-trione: An efficient route for the one-pot synthesis of sterically congested 2,2-disubstituted indane-1,3-dione derivatives. J. Braz. Chem. Soc. 2009, 20, 309.
14. Souldozi, A. Iminophosphorane-mediated one-pot synthesis of 1,3,4-oxadiazole derivatives. Arkivoc 2008, 235.
15. Ramazani, A.; Noshiranzadeh, N. Reaction between 1,3-dicarbonyl- containing CH acids and dialkyl acetylenedicarboxylates in the presence of silica gel in solvent-free conditions: An efficient method for the synthesis of electron-poor alkenes and pyranes. Synth. Commun. 2009, 39, 1204.
16. Ramazani, A.; Noshiranzadeh, N.; Slepokura, K.; Lis, T. Novel stereoselective synthesis of densely functionalized 2H-indeno[2,1-b]furans. Synth. Commun. 2008, 38, 1560.
17. Ramazani, A.; Kardan, M.; Noshiranzadeh, N.; Reaction between imides and electron-poor acetylenic esters in the presence of dipotassium hydrogen phosphate powder in solvent-free conditions: An efficient method for the synthesis of electron-poor N-vinyl imides. Synth. Commun. 2008, 38, 383.
18. Yavari, I.; Ramazani, A. An efficient one-pot synthesis of dialkyl 3H-naphtho[2,1, b]pyran-2,3-dicarboxylates mediated by vinyl triphenylphosphonium salt. Synth. Commun. 1997, 27, 1385.
19. Ramazani, A.; Noshiranzadeh, N.; Ghamkhari, A.; Sepokura, K.; Lis, T. One-pot diaster-eoselective synthesis of densely functionalized 2H-indeno[2,1-b]furans. Single-crystal X-Ray structure of dimethyl 8,8a-dihydro-8-oxo-8a-(2,2,2-trichloroethoxy)-2H-indeno[2,1-b]furan-2, 3-dicarboxylate. Helv. Chim. Acta 2008, 91, 2252.
20. Ramazani, A.; Kazemizadeh, A. R.; Ahmadi, E.; Noshiranzadeh, N.; Souldozi, A. Synthesis and reactions of stabilized phosphorus ylides. Curr. Org. Chem. 2008, 12, 59.
21. Anary-Abbasinejad, M.; Mosslemin, M. H.; Tahan, S.; Anaraki-Ardakani, H. Synthesis of unsaturated amidines by three component reaction of alkylisocyanides, dialkyl acetyle-nedicarboxylates, and aromatic amides. J. Chem. Res. 2006, 170.
22. Anary-Abbasinejad, M.; Mosslemin, M. H.; Anaraki-Ardakani, H.; Tahan, S. Synthesis of unsaturated amidine derivatives by three component reaction of alkyl isocyanides, dialkyl acetylenedicarboxylates and pyrrole or indole. J. Chem. Res. 2006, 306.
23. Mosslemin, M. H.; Nateghi, M. R.; Hassanabadi, A.; Zare, M. Three-component reaction of alkyl isocyanides, dialkyl acetylenedicarboxylates and furan-2-carboxylic acid arylidene-hydrazides. J. Chem. Res. 2010, 178.
24. Anary-Abbasinejad, M.; Anaraki-Ardakani, H.; Rastegari, F.; Hassanabadi, A. One-pot synthesis of functionalized keteneimines by three component reaction of isocyanides, dialkyl acetylenedicarboxylates, and 4-phenylaminocoumarin. J. Chem. Res. 2007, 602.