You are here

1,3-DİSUBSTİTUE-2,3-DİHİDRO-1H-NAFT-[1,3]OKSAZİN BİLEŞİKLERİNİN SENTEZİ

SYNTHESIS OF 1,3-DISUBSTITUED-2,3-DIHYDRO-1H-NAFT[1,3] OXAZİNE COMPOUNDS

Journal Name:

Publication Year:

Keywords (Original Language):

Author NameUniversity of AuthorFaculty of Author
Abstract (2. Language): 
In this study, Betti's classical procedur[1], a Mannich-type aminoalkylation reaction of 2- naphtol with furan- 2-, furan-3-, thiphene-3-, pyridine-4- and naptalene-2-carbaldehydes was applied in the presence of ammonia. 1,3-disubstituted-2,3-dihydro-1H- naphtoxazines were synthesized The structures of the obtained new compounds have been clarified by spectroscopic methods (FTIR, 1 H NMR, 13C NMR and MS) and confirmed with elemental analysis results.
Abstract (Original Language): 
Bu çalışmada Betti’nin klasik metodu uygulanarak[1], 2-naftolün susuz metanol amonyaklı ortamda furan-2- , furan-3-, tiyofen-3-, piridin-4- ve naftalen-2-karbaldehidleri ile Mannich tip aminoalkilasyonu gerçekleştirildi. 1,3-disubstitüe-2,3-dihidro-1H-naftoksazinler sentezlendi. Sentezlenen yeni bileşiklerin yapıları FTIR, 1 HNMR, 13CNMR ve kütle spektroskopik yöntemlerinden yararlanarak aydınlatıldı ve elementel analiz sonuçlarıyla kesinlik kazandırıldı.

REFERENCES

References: 

[1] Betti, M.; “β-Naphtholphenylaminomethane”, Org. Synth. Coll. Vol., 1,381-383 ,1941.
[2] Adib, M.; Sheibani, E.; Mostofi, M.; Ghanbary, K.; Bijanzadeh, H. R.; “Efficient highly
diastereoselective synthesis of 1,8a-dihydro-7H-imidazo[2,1-b][1,3]oxazines”,
Tetrahedron, 62, 3435-3438, 2006.
[3] Kurz , T.; “Synthesis of Novel Pyrido[2,3-e][1,3]oxazines”, Tetrahedron, 61, 3091-3096,
2005.
[4] Cimarelli, C.; Mazzanti, A.; Palmieri, G.; Volpini, E.; “Solvent-free asymmetric
aminoalylation of electron-rich aromatic compounds: stereoselective synthesis of
aminoalkylnaphthols by crystallization-induced asymetric transformation”, J.Org. Chem.,
66, 4759 -4765, 2001.
[5] Szatmari, I.; Martinek, T.A.; Lazar L.; Fülop, F.; “Substituent effects in the ring-chain
tautomerism of 1,3-diaryl-2,3-dihidro-1H-napht[1,2-e][1,3]oxazines”, Tetrahedron , 59,
2877-2884, 2003.
[6] Szatmari I., Lazar L., Fülop F.;“Microwave-assisted, solvent-free synthesis of 1-(α- or β-
hydroxynapthyl)-1,2,3,4-tetrahydroisoquinolines by the Mannich reaction”, Tetrahedron
Letters, 47,3881-3883, 2006.
[7] Szatmari, I.; Martinek, T.A; Lazar L. ; Fülop, F.; “Synthesis of 2,4-Diaryl-3,4-dihydro-
2H-naphth[2,1-e][1,3]oxazines and study of the effects of the substituents on Their ringchain tautomerism”, Eur. J. Org. Chem., 2231- 2238, 2004.
[8] Heydenreich,M., Koch, A., Klod S., Szatmari, I., Fülop, F..Kleinpeter E.; “Synthesis and
comformational analysis of naphth[1’,2’:5,6][1,3]oxazino[3,2-c][1,3]benzoxazine and
naphth[1’,2’:5,6][1,3] oxazino[3,4-c][1,3]benzoxazine derivatives”, Tetrahedron,
62,11081-11089, 2006.
[9] Sainsbury, M.; “ Rodd’s Chemistry of Carbon Compounds Vol. IV. Heterocyclic
Compounds. Path H”, 2nd Ed. S.Coffey, Elsevier Scientific Public Comp. The
Netherlands, 1978.
[10] Poel H.V.D., Guillaumet G., Viaud-Massuard M.C.; “Synthesis of 6,7,8,9-
tetrahydropyrido[2,3-b]indolizine and 3,4-dihydro-2H-pyrido[2’,3’:4,5]pyrrolo[2,1-
b][1,3]oxazine derivatives as new melatonin receptor ligands”, Tetrahedron Letters, 43,
1205-1208, 2002.
[11] Meng X., Zhu W., Guo Z., Wang J., Tian H., “Highly Stable and Fluorescent Switching
Spirooxazines”, Tetrahedron, 62, 9840-9845, 2006.
[12] Yıldırım A., Kiskan B., Demirel A.L., Yağcı Y.; “Synthesis, characterization and
properties of naphtoxazine-functional poly(propyleneoxide)s”, European Polymer Journal,
42, 3006-3014, 2006.
[13] Zhang P., Terefenko E.A. Fensome A., Wrobel J., Winneker R., Zhang Z.; “Novel 6-
Aryl-1,4-dihydrobenzo[d][1,3]oxazine-2-thiones as Potent, Selective, and Orally Active
Nonsteroidal Progesterone Receptor Agonists”, Bioorganic&Medicinal Chemistry, 13,
313-1316, 2003.
[14] Öcal N., Aydoğan F., “Organik Laboratuar Teknikleri”,YTÜ Basım –Yayın Merkezi,
İstanbul, 2004.
[15] Furniss B. S., Hannaford A.J., Rogers V., Smith P.W. G. and Tatchell A.R., “Vogel’s
Textbook of Practical Organic Chemistry”, 4Th ed., Longman, London ,1978.

Thank you for copying data from http://www.arastirmax.com