Synthesis of 1,5-Benzodiazepines with Unusual Substitution Pattern from Chalcones Under Solvent-Free Microwave Irradiation Conditions

被引：12

作者：

Escobar, Carlos A. ^{[1
]}

Donoso-Tauda, Oscar ^{[1
]}

Araya-Maturana, Ramiro ^{[2
]}

Sicker, Dieter ^{[3
]}

机构：

[1] Univ Andres Bello, Dept Ciencias Quim, Lab Recursos Nat, Santiago, Chile

[2] Univ Chile, Fac Chem & Pharmaceut Sci, Dept Organ & Phys Chem, Santiago, Chile

[3] Univ Leipzig, Inst Organ Chem, Leipzig, Germany

来源：

SYNTHETIC COMMUNICATIONS | 2009年 / 39卷 / 01期

关键词：

Alumina; benzodiazepine; chalcone; microwave irradiation; solvent-free synthesis; DERIVATIVES;

D O I：

10.1080/00397910802372517

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,5-Benzodiazepines have been synthesized from the corresponding 20-hydroxychalcones [1-(2-hydroxyphenyl)-3-aryl-2-propen-1-ones] and o-phenylene-diamine, both in methanol, under reflux and under solvent-free microwave irradiation conditions on alumina. The latter method proved to be advantageous.

引用

页码：166 / 174

页数：9

共 13 条

[1] A simple and new method for the synthesis of 1,5-benzodiazepine derivatives on a solid surface [J].

Balakrishna, MS ;

Kaboudin, B .

TETRAHEDRON LETTERS, 2001, 42 (06) :1127-1129

[2] Two-step synthesis of β-alkyl chalcones and their use in the synthesis of 3,5-diaryl-5-alkyl-4,5-dihydropyrazoles [J].

Cox, CD ;

Breslin, MJ ;

Mariano, BJ .

TETRAHEDRON LETTERS, 2004, 45 (07) :1489-1493

[3]

DHAR DN, 1961, J INDIAN CHEM SOC, V38, P823

[4] 4-(2-Hydroxyphenyl)-2-phenyl-2,3-dihydro-1H-1,5-benzodiazepine and the 2-(2,3-dimethoxyphenyl)-, 2-(3,4-dimethoxyphenyl)- and 2-(2,5-dimethoxyphenyl)-substituted derivatives [J].

Escobar, Carlos A. ;

Donoso-Tauda, Oscar ;

Araya-Maturana, Ramiro ;

Vega, Andres .

ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 2007, 63 (o426-o430) :O426-O430

[5] Synthesis and crystal structure analysis of a 2,4-diaryl-2,3-dihydro-1H-1,5-benzodiazepine [J].

Hormaza, A ;

Schollmeyer, D ;

Meier, H .

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2004, 59 (01) :73-76

[6] Solvent-free synthesis of 1,5-benzothiazepines and benzodiazepines on inorganic supports [J].

Kodomari, M ;

Noguchi, T ;

Aoyama, T .

SYNTHETIC COMMUNICATIONS, 2004, 34 (10) :1783-1790

[7] Synthesis, IR-, NMR- and X-ray investigations on some novel N-hetaryl-dihydro-pyrazolyl ferrocenes.: Study on ferrocenes, part 16 [J].

Kudar, V ;

Zsoldos-Mády, V ;

Simon, K ;

Csámpai, A ;

Sohár, P .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (17) :4018-4026

[8] An efficient method for the synthesis of 1,5-benzodiazepine derivatives under microwave irradiation without solvent [J].

Pozarentzi, M ;

Stephanidou-Stephanatou, J ;

Tsoleridis, CA .

TETRAHEDRON LETTERS, 2002, 43 (09) :1755-1758

[9] Electrochemical approach to the radical anion formation from 2′-hydroxy chalcone derivatives [J].

Quintana-Espinoza, P ;

Yáñez, C ;

Escobar, CA ;

Sicker, D ;

Araya-Maturana, R ;

Squella, JA .

ELECTROANALYSIS, 2006, 18 (05) :521-525

[10] An efficient synthesis of 1,5-benzodiazepine derivatives catalyzed by a solid superacid sulfated zirconia [J].

Reddy, BM ;

Sreekanth, PM .

TETRAHEDRON LETTERS, 2003, 44 (24) :4447-4449

← 1 2 →