새로운 2,4-이치환된 티아졸들과 2-(Allylidenehydrazono)-thiazolo[5,4-b]quinoxaline 유도체들의 합성

김종근; 배선건; Jong-Geun Kim; Sun Kun Bae

Journal of the Korean Industrial and Engineering Chemistry, Vol.20, No.2, 134-139, April, 2009

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새로운 2,4-이치환된 티아졸들과 2-(Allylidenehydrazono)-thiazolo[5,4-b]quinoxaline 유도체들의 합성

Synthesis of New 2,4-Disubstituted Thiazoles and 2-(Allylidenehydrazono)-thiazolo[5,4-b]quinoxaline Derivatives

김종근, 배선건^†

군산대학교 화학과

Jong-Geun Kim, and Sun Kun Bae^†

Department of Chemistry, Kunsan National University, Kunsan 573-701, Korea

E-mail:

초록

(E)-3-(Aryl)acrylaldehyde 유도체들 (1a∼1e)과 thiosemicarbazide 축합반응으로 일련의 알릴리덴치오세미카르바존 화합물 (2a∼2e)을 45∼85%로 얻었다. 이 화합물들을 2,4'-dibromoacetophenone와 2,3-dichloroquinoxaline로 처리하여 각각 2,4-이 치환 티아졸류(3a∼3e)와 2-[(E)-3-(aryl)allylidenehydrazone]thiazolo[5,4-b]quinoxaline류 (4a∼4e)를 좋은 수율로 합성하였다. 새로이 합성한 모든 화합물들의 구조들은 IR과 1H-NMR 분광학 자료로 확인하였다.

A series of allylidenethiosemicarbazone compounds (2a∼2e) were obtained in 45∼85% by condensing (E)-3-(aryl)acrylaldehyde (1a∼1e) with thiosemicarbazide. Theses compounds on treatment of 2,4'-dibromoacetophenone and 2,3-dichloroquinoxaline yielded 2,4-disubstituted thiazoles (3a∼3e) and 2-[(E)-3-(aryl)allylidenehydrazono]thiazolo[5,4-b]quinoxaline (4a∼4e) in good yield respectively. The structures of all the newly synthesized compounds were identified by IR and 1H-NMR spectral data.

Keywords:thiosemicarbazide;2,4'-dibromacetophenone;2,3-dichloroquinoxaline;thiazole

[References]

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[1] Gu XH, Wan XZ, Jiang B, Bioorg. Med. Chem. Lett., 9, 569 (1999)

[2] Kazzouli SE, Berteina-Raboin S, Mouaddib A, Guillaumet G, Tetrahedron Lett., 43, 3193 (2002)

[3] Hargrave KD, Hess FK, Olive JT, J. Med. Chem., 26, 1158 (1983)

[4] Patt WC, Hamilton HW, Taylor MD, Rayan MJ, Taylor Jr. DG, Connolly CJC, Doberty AM, Klutchko SR, Sircar I, Olson SJC, J. Med. Chem., 35, 2562 (1992)

[5] Sharma PK, Sawnhney SN, Gupta A, Sinh GB, Bani S, Indian J. Chem., 33, 376 (1990)

[6] Jaen JC, Wise LD, Caprathe BW, Tecle H, Bergmeie S, Humblet CC, Heffner TG, Meltzner LT, Pugsley TA, J. Med. Chem., 33, 311 (1990)

[7] Vicini P, Geronikaki A, Anastsia K, Incerti M, Zani F, Bioorg. Med. Chem., 14, 3859 (2006)

[8] Kalkhambkar RG, Kulkarni GM, Shivkumar H, Rao RN, Eur. J. Med. Chem., 42, 1272 (2007)

[9] Franklin PX, Pillai AD, Rathod PD, Yerande S, Nivsarkar M, Vasu KK, Sundarsanam V, Eur. J. Med. Chem., 43, 129 (2008)

[10] Karegoudar P, Karthikeyan MS, Prasad DJ, Hahalinga M, Holla BS, Kumari NS, ibid., 43, 261 (2008)

[11] Bae SK, Yeon YH, J. Korean Ind. Eng. Chem., 13(5), 486 (2002)

[12] Li Z, Yang Q, Qian X, Bioorg. Med. Chem., 13, 3149 (2005)

[13] Qian X, Li Z, Yang Q, Bioorg. Med. Chem., 15, 6846 (2007)

[14] Vicini P, Geronikaki A, Incerti M, Zani F, Dearden J, Hewitt M, Bioorg. Med. Chem., 16, 3714 (2008)

[15] Novak L, Rohaly J, Szantay C, OPP BRIEFS, 31, 693 (1999)

[16] Sinha SC, Dutta S, Sun J, Tetrahedron Lett., 41, 8243 (2002)

[17] Aoyama T, Murata S, Sukuki Y, Komodori M, Tetrhedron, 62, 1 (2006)

[18] Narender M, Reddy MS, Sridhra R, Nageswar YVD, Rao KR, Tetrahedron Lett., 46, 5953 (2005)