Synthesis of 4-methylene-1,3-naphthoxazines by the reaction of imines with triphosgene

Synthetic Communications

Volumn 41, Issue 19, 2011, Pages 2952-2958

  Al Bogami, Abdullah Saad ^a  

^a KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

1,3 naphthoxazines; 2 Acetyl 1 naphthol; Amines; Imines; Microwave irradiation; Triphosgene

Indexed keywords

1 NAPHTHOL DERIVATIVE; 2 (1 BUTYLIMINO ETHYL)NAPHTHALEN 1 OL; 2 (1 HEPTYLIMINO ETHYL)NAPHTHALEN 1 OL; 2 (1 HEXYLIMINO ETHYL)NAPHTHALEN 1 OL; 2 (1 ISOBUTYLIMINO ETHYL)NAPHTHALEN 1 OL; 2 (1 PROPYLIMINO ETHYL)NAPHTHALEN 1 OL; 2 ACETYL 1 NAPHTHOL; 3 BUTYL 4 METHYLENE 3,4 DIHYDRO NAPHTHO[2,1 E][1,3]OXAZINE 2 ONE; 3 HEPTYL 4 METHYLENE 3,4 DIHYDRO NAPHTHO[2,1 E][1,3]OXAZINE 2 ONE; 3 HEXYL 4 METHYLENE 3,4 DIHYDRO NAPHTHO[2,1 E][1,3]OXAZINE 2 ONE; 3 ISOBUTYL 4 METHYLENE 3,4 DIHYDRO NAPHTHO[2,1 E][1,3]OXAZINE 2 ONE; 4 METHYLENE 3 PROPYL 3,4 DIHYDRO NAPHTHO[2,1 E][1,3]OXAZINE 2 ONE; ALIPHATIC AMINE; IMINE; NAPHTHOXAZINE DERIVATIVE; PHOSGENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; INFRARED RADIATION; SYNTHESIS;

EID: 79959955259     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.515767     Document Type: Article

References (13)

1. Eckert, H.; Forster, B. Triphosgene, a crystalline phosgene substitute. Angew. Chem., Int. Ed. Engl. 1987, 26, 894.
2. Di Santo, R.; Costi, R.; Artico, M.; Massa, S.; Morangiu, M. E.; Loi, A. G.; De Montis, A.; La Colla, P. 1,2,5-Benzothiadiazepine and pyrrolo[2,1d][1,2,5]benzothiadiazepine derivatives with specific anti-human immunodeficiency virus type 1 activity. Antiviral Chem. Chemother. 1998, 9, 127.
3. Chung, Y. J.; Jung, Y. S.; Seong, C. M.; Park, N. S. An efficient synthesis of 3-substituted quinazolones. Bull. Korean Chem. Soc. 1998, 19, 1117.
4. Nefzi, A.; Otresh, J. M.; Giulianotti, M.; Hougten, R. A. Efficient solid-phase synthesis of 3,5-disubstituted hydantoins. Tetrahedron Lett. 1998, 39, 8199.
5. Li, Z.; Zhang, Y. Low-valent titanium-induced cyclization of dimeric dianions of anils with triphosgene: A safe and efficient method for the syntheses of substituted imidazolidine 2-ones. Synth. Commun. 2002, 32, 2613.
6. Krishnaswamy, D.; Govande, V. V.; Gumaste, V. K.; Bhawal, B. M.; Deshmukh, A. R. A. S. Triphosgene: A versatile reagent for the synthesis of azetidin-2-ones. Tetrahedron 2002, 58, 2215.
7. Albogami, A. S.; Almajid, A. M.; Al-Saad, M. A.; Mosa, A. M.; Almazroa, S. A.; Alkhathlan, H. Z. Cyclization of hydrazones of 2-acetyl-1-naphthol and 1-acetyl-2-naphthol with triphosgene: Synthesis of spiro naphthoxazine dimers benzoxazinones. Molecules 2009, 14, 2147.
8. Eynde, J. J. V.; Fromont, D. Microwave-mediated synthesis of imines from heterocyclic amines and aldehydes. Bull. Soc. Chim. Belg. 1997, 106, 393.
9. Yang, H.; Sun, W.; Li, Z. Solvent-free synthesis of salicylaldimines assisted by microwave. Synth. Commun. 2002, 32, 2395.
10. Yuedan, W.; Haijian, Y. Rapid synthesis of salicylaldehydimines without solvent under microwave irradiation. Zhongnan Minzu Daxue Xuebao, Ziran Kexueban 2007, 26 (4), 1.
11. Hayes, B. L. Microwave Synthesis Chemistry at the Speed of Light; CEM Publishing: Matthews, NC, 2002.
12. Alkhathlan, H. Z. A one-pot synthesis of 1,3-benzoxazines. Synth. Commun. 2004, 34, 71.
13. Alkhathlan, H. Z.; Al-Saad, M. A.; Al-Hazimi, H. M.; Al-Farhan, K. A.; Mousa, A. A. Synthesis and x-ray crystal structures of novel spiro-1,3-benzoxazine dimmers. J. Chem. Res. Synop. 2002, 473.