A Tandem One-Pot, Microwave-Assisted Synthesis of Regiochemically Differentiated 1,2,4,5-Tetrahydro-1 4-benzodiazepin-3-ones

被引：85

作者：

De Silva, Ravindra A. ^{[1
]}

Santra, Soumava ^{[1
]}

Andreana, Peter R. ^{[1
]}

机构：

[1] Wayne State Univ, Dept Chem, Detroit, MI 48202 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 20期

关键词：

D O I：

10.1021/ol801841m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot, two-step synthesis of the title compounds employs a multicomponent Ugi condensation reaction, microwave irradiation, and Fe(0) as a reductant. Two pathways are accessible; both routes utilize bifunctional, o-nitro-substituted arenes leading to either C2, N4, C5 substitution (A) or C2, N4 substitution (B).

引用

页码：4541 / 4544

页数：4

共 28 条

[1] Reduction of nitro aromatic compounds by zero-valent iron metal [J].

Agrawal, A ;

Tratnyek, PG .

ENVIRONMENTAL SCIENCE & TECHNOLOGY, 1996, 30 (01) :153-160

[2] A versatile synthesis of fused triazolo derivatives by sequential Ugi/alkyne-azide cycloaddition reactions [J].

Akritopoulou-Zanze, I ;

Gracias, V ;

Djuric, SW .

TETRAHEDRON LETTERS, 2004, 45 (46) :8439-8441

[3] A new synthesis of the GPIIb/IIIa receptor antagonist SB-214857-A [J].

Andrews, IP ;

Atkins, RJ ;

Badham, NF ;

Bellingham, RK ;

Breen, GF ;

Carey, JS ;

Etridge, SK ;

Hayes, JF ;

Hussain, N ;

Morgan, DO ;

Share, AC ;

Smith, SAC ;

Walsgrove, TC ;

Wells, AS .

TETRAHEDRON LETTERS, 2001, 42 (29) :4915-4917

[4] A simple route to tetrahydro-1,4-benzodiazepin-3-ones bearing diverse N1, N4, and C10 functionalization [J].

Clement, EC ;

Carlier, PR .

TETRAHEDRON LETTERS, 2005, 46 (21) :3633-3635

[5] Design, synthesis, biological evaluation, and molecular modeling studies of TIBO-like cyclic sulfones as non-nucleoside HIV-1 reverse transcriptase inhibitors [J].

Di Santo, Roberto ;

Costi, Roberta ;

Artico, Marino ;

Ragno, Rino ;

Lavecchia, Antonio ;

Novellino, Ettore ;

Gavuzzo, Enrico ;

La Torre, Francesco ;

Cirilli, Roberto ;

Cancio, Reynel ;

Maga, Giovanni .

CHEMMEDCHEM, 2006, 1 (01) :82-95

[6]

Fox B.A., 1973, ORG SYNTH, V5, P346

[7] Conformational preferences in a benzodiazepine series of potent nonpeptide fibrinogen receptor antagonists [J].

Keenan, RM ;

Callahan, JF ;

Samanen, JM ;

Bondinell, WE ;

Calvo, RR ;

Chen, LC ;

DeBrosse, C ;

Eggleston, DS ;

Haltiwanger, RC ;

Hwang, SM ;

Jakas, DR ;

Ku, TW ;

Miller, WH ;

Newlander, KA ;

Nichols, A ;

Parker, MF ;

Southhall, LS ;

Uzinskas, I ;

Vasko-Moser, JA ;

Venslavsky, JW ;

Wong, AS ;

Huffman, WF .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (04) :545-559

[8] Synthesis and protein kinase C binding activity of benzolactam-V7 [J].

Ma, DW ;

Wang, GQ ;

Wang, SM ;

Kozikowski, AP ;

Lewin, NE ;

Blumberg, PM .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (10) :1371-1374

[9] CuI-catalyzed coupling reaction of β-amino acids or esters with aryl halides at temperature lower than that employed in the normal Ullmann reaction.: Facile synthesis of SB-214857 [J].

Ma, DW ;

Xia, CF .

ORGANIC LETTERS, 2001, 3 (16) :2583-2586

[10] Enantiospecific synthesis of SB 214857, a potent, orally active, nonpeptide fibrinogen receptor antagonist [J].

Miller, WH ;

Ku, TW ;

Ali, FE ;

Bondinell, WE ;

Calvo, RR ;

Davis, LD ;

Erhard, KF ;

Hall, LB ;

Huffman, WF ;

Keenan, RM ;

Kwon, C ;

Newlander, KA ;

Ross, ST ;

Samanen, JM ;

Takata, DT ;

Yuan, CK .

TETRAHEDRON LETTERS, 1995, 36 (52) :9433-9436

← 1 2 3 →