One-pot synthesis of novel pyrrolo-1,4-benzoxazines via a three-component reaction of 2-amino phenols, acetylenic esters and nitrostyrene derivatives

Chinese Chemical Letters

Volumn 25, Issue 1, 2014, Pages 123-126

  Moradi, Loghman ^a   Piltan, Mohammad ^b   Rostami, Hedieh ^a  

^a UNIVERSITY OF KURDISTAN   (Iran)

^b ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

2 Amino phenol; Acetylenic esters; Nitrostyrene; Pyrrolo 1,4 benzoxazine

Indexed keywords

EID: 84892567220     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2013.10.009     Document Type: Article

References (17)

1. A. Dömling Recent developments in isocyanide based multicomponent reactions in applied chemistry Chem. Rev. 106 2006 17 89
2. B. Achari, S.B. Mandal, P.K. Dutta, and C. Chowdhury Perspectives on 1,4-benzodioxins, 1,4-benzoxazines and their 2,3-dihydro derivatives Synlett 2004 2449 2467
3. J.H. Wu, F.R. Chang, and K. Hayashi et al. Antitumor agents. part 218: cappamensin a, a new in vitro anticancer principle, from capparis sikkimensis Biorg. Med. Chem. Lett. 13 2003 2223 2225
4. J. Bergman, S. Rosenzweig-Lipson, and R.D. Spealman Differential effects of dopamine D1 and D2 receptor agonists on schedule-controlled behavior of squirrel monkeys J. Pharmacol. Exp. Ther. 273 1995 40 48
5. P.J. Rybczynski, R.E. Zeck, and D.W. Combs et al. Benzoxazinones as PPARγ agonists. Part 1: SAR of three aromatic regions Biorg. Med. Chem. Lett. 13 2003 2359 2362
6. G. Campiani, A. Garofalo, and I. Fiorini et al. Pyrrolo[2,1-c][1,4] benzothiazines: synthesis, structure-activity relationships, molecular modeling studies, and cardiovascular activity J. Med. Chem. 38 1995 4393 4410
7. D.S. Snyder, L. Tradtrantip, C. Yao, M.J. Kurth, and A.S. Verkman Potent, metabolically stable benzopyrimido-pyrrolo-oxazine-dione (BPO) CFTR inhibitors for polycystic kidney disease J. Med. Chem. 54 2011 5468 5477
8. X.Q. Xie, X.W. Han, J.Z. Chen, M. Eissenstat, and A. Makriyannis High-resolution NMR and computer modeling studies of the cannabimimetic aminoalkylindole prototype WIN-55212-2 J. Med. Chem. 42 1999 4021 4027
9. S. Kurhade, R.D. Kaduskar, and B. Dave et al. Synthesis of a novel tetracyclic azaindolo[2,1-c][1,4]benzoxazine ring system Tetrahedron Lett. 52 2011 1874 1877
10. A. Santra, G. Guchhait, and A.K. Misra Efficient acylation and sulfation of carbohydrates using sulfamic acid, a mild, eco-friendly catalyst under organic solvent-free conditions Green Chem. 13 2011 1345 1351
11. I. Yavari, A. Mirzaei, L. Moradi, and A. Mokhtarporiani-Sanandaj Efficient synthesis of trialkyl (E)-3-{3-Oxo-2-3,4-dihydro-2-(1H)- quinoxalinylidene}prop-1-ene-1,2,3-tricarboxylates Synth. Commun. 37 2007 1195 1200
12. I. Yavari, and L. Moradi Synthesis of isoxazoles through the reaction of activated acetylenes and alkyl 2-nitroethanoates in the presence of triphenylphosphine Tetrahedron Lett. 47 2006 1627 1629
13. I. Yavari, M. Piltan, and L. Moradi Synthesis of pyrrolo[2,1-a] isoquinolines from activated acetylenes, benzoylnitromethanes, and isoquinoline Tetrahedron 65 2009 2067 2071
14. M. Piltan, I. Yavari, L. Moradi, and S.A. Zarei PEG-Mediated catalyst-free expeditious synthesis of functionalized benzene/biaryl and fluoren-9-one derivatives from activated acetylenes and 1,3-diones J. Korean Chem. Soc. 56 2012 316 321
15. J. Christoffers, H. Frey, and A. Rosiak B. Pleitker, Iron Catalysis in Organic Chemistry 2008 Wiley-VCH Weinheim 217 244
16. N. Kawahara, T. Shimamori, T. Itoh, and H. Ogura Thermal reactions of o-aminophenols and dimethyl actylenedicarboxylate Heterocycles 24 1986 2803 2807
17. I. Yavari, A. Mirzaei, and L. Moradi Efficient synthesis of dialkyl (2Z)-2-[(E)-1-Aryl-2-(3-arylquinoxalin-2-yl)ethenyl]but-2-enedioates Helv. Chim. Acta 89 2006 2825 2829