Development of Safe One-Pot Synthesis of N-1-and C-2-Substituted Benzimidazole via Reductive Cyclization of o-Nitroarylamine Using Na2S2O4

被引：30

作者：

Oda, Shinichi ^{[1
]}

Shimizu, Hideki ^{[1
]}

Aoyama, Yasunori ^{[1
]}

Ueki, Tatsuo ^{[1
]}

Shimizu, Sumio ^{[1
]}

Osato, Hiroshi ^{[1
]}

Takeuchi, Yoshiyuki ^{[1
]}

机构：

[1] Shionogi & Co Ltd, Chem Dev Ctr, CMC Dev Labs, Amagasaki, Hyogo 6600813, Japan

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2012年 / 16卷 / 01期

关键词：

NITRO-COMPOUNDS; THERMAL HAZARDS; POLYMERASE; INHIBITORS; NITROANILINES; DERIVATIVES;

D O I：

10.1021/op200251c

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

We report that the reductive cyclization of o-nitroarylamine with aldehyde using sodium dithionite (Na2S2O4) could be accelerated by addition of H2O, which made it possible to control the heat release of the reaction by semibatch-type operation. Safety evaluation was performed using DSC, ARSST, in situ IR analysis, and Multimax.

引用

页码：96 / 101

页数：6

共 15 条

[1] Safety evaluation of an unexpected incident with a nitro compound [J].

Barbas, Rafael ;

Botija, Manuel ;

Camps, Helena ;

Portell, Anna ;

Prohens, Rafel ;

Puigjaner, Cristina .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (06) :1131-1134

[2] Improved replicon cellular activity of non-nucleoside allosteric inhibitors of HCVNS5B polymerase:: From benzimidazole to indole scaffolds [J].

Beaulieu, Pierre L. ;

Gillard, James ;

Bykowski, Darren ;

Brochu, Christian ;

Dansereau, Nathalie ;

Duceppe, Jean-Simon ;

Haché, Bruno ;

Jakalian, Araz ;

Lagacé, Lisette ;

LaPlante, Steven ;

McKercher, Ginette ;

Moreau, Elaine ;

Perreault, Stphane ;

Stammers, Timothy ;

Thauvette, Louise ;

Warrington, Jeff ;

Kukolj, George .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (19) :4987-4993

[3] Non-nucleoside inhibitors of the hepatitis C virus NS5B polymerase:: discovery and preliminary SAR of benzimidazole derivatives [J].

Beaulieu, PL ;

Bös, M ;

Bousquet, Y ;

Fazal, G ;

Gauthier, J ;

Gillard, J ;

Goulet, S ;

LaPlante, S ;

Poupart, MA ;

Lefebvre, S ;

McKercher, G ;

Pellerin, C ;

Austel, V ;

Kukolj, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (01) :119-124

[4]

FUJISHITA T, 2005, Patent No. 2005121132

[5] Runaway reaction hazards in processing organic nitro compounds [J].

Gustin, JL .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1998, 2 (01) :27-33

[6] Benzimidazole derivatives bearing substituted biphenyls as hepatitis C virus NS5B RNA-dependent RNA polymerase inhibitors: Structure-activity relationship studies and identification of a potent and highly selective inhibitor JTK-109 [J].

Hirashima, Shintaro ;

Suzuki, Takayoshi ;

Ishida, Tomio ;

Noji, Satoru ;

Yata, Shinji ;

Ando, Izuru ;

Komatsu, Masakazu ;

Ikeda, Satoru ;

Hashimoto, Hiromasa .

JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (15) :4721-4736

[7] Accelerated process development of pharmaceuticals: Selective catalytic hydrogenations of nitro compounds containing other functionalities [J].

Hoogenraad, M ;

van der Linden, JB ;

Smith, AA ;

Hughes, B ;

Derrick, AM ;

Harris, LJ ;

Higginson, PD ;

Pettman, AJ .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2004, 8 (03) :469-476

[8]

KAZAKOV A, 1992, BULG T NAUCHNOIZSLED, V18, P17

[9] Thermal hazards and safe scale-up of reactions containing dimethyl sulfoxide [J].

Lam, T. T. ;

Vickery, T. ;

Tuma, Linda .

JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY, 2006, 85 (01) :25-30

[10] SODIUM DITHIONITE REDUCTION OF NITROARENES USING VIOLOGEN AS AN ELECTRON PHASE-TRANSFER CATALYST [J].

PARK, KK ;

OH, CH ;

JOUNG, WK .

TETRAHEDRON LETTERS, 1993, 34 (46) :7445-7446

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