A HCN-based reaction under microreactor conditions: industrially feasible and continuous synthesis of 3,4-diamino-1H-isochromen-1-ones

Microreactor technology has been studied as a suitable process to produce chemicals via multicomponent reactions. In this study, efforts were made to produce 3,4-diamino-1H-isochromen-1-ones. Based on a known reaction procedure, using in situ generated HCN, a safe reaction setup was created to avoid the release of the hazardous gas during the process. The 3,4-diamino-1H-isochromen-1-ones were produced continuously in moderate to good yields.

[1]  Masaaki Sato,et al.  Continuous microflow synthesis of butyl cinnamate by a Mizoroki-Heck reaction using a low-viscosity ionic liquid as the recycling reaction medium , 2004 .

[2]  K. Jensen.  Microreaction engineering * is small better? , 2001 .

[3]  D. Basavaiah,et al.  Recent advances in the Baylis-Hillman reaction and applications. , 2003, Chemical reviews.

[4]  H. Löwe,et al.  Chemistry in microstructured reactors. , 2004, Angewandte Chemie.

[5]  D. Agar,et al.  The capillary-microreactor: a new reactor concept for the intensification of heat and mass transfer in liquid–liquid reactions , 2003 .

[6]  T. Opatz,et al.  Facile preparation of 3-amino-4-(arylamino)-1H-isochromen-1-ones by a new multicomponent reaction , 2005 .

[7]  Michael Arend,et al.  Modern Variants of the Mannich Reaction. , 1998, Angewandte Chemie.

[8]  Paul Watts,et al.  Continuous flow reactors for drug discovery. , 2003, Drug discovery today.

[9]  C. Stevens,et al.  Continuous Synthesis of Tri‐ and Tetrasubstituted Imidazoles via a Multicomponent Reaction under Microreactor Conditions , 2006 .

[10]  K. Mae,et al.  Room-temperature Swern oxidations by using a microscale flow system. , 2005, Angewandte Chemie.

[11]  F Feigl,et al.  Replacement of benzidine by copper ethylacetoacetate and tetra base as spot-test reagent for hydrogen cyanide and cyanogen. , 1966, The Analyst.

[12]  Frank J. Villani,et al.  Application of Microreactor Technology in Process Development , 2004 .

[13]  C. Stevens,et al.  Study of the Baylis-Hillman reaction in a microreactor environment : first continuous production of Baylis-Hillman adducts , 2006 .

[14]  J. Sapi,et al.  Indole based multicomponent reactions towards functionalized heterocycles , 2004 .

[15]  P. D. Rao,et al.  THE BAYLIS-HILLMAN REACTION : A NOVEL CARBON-CARBON BOND FORMING REACTION , 1996 .

[16]  A. Wolf,et al.  Microreactors, a new efficient tool for optimum reactor design , 2001 .

[17]  Klavs F. Jensen,et al.  Microfabricated multiphase packed-bed reactors : Characterization of mass transfer and reactions , 2001 .

[18]  Albert van den Berg,et al.  On-microchip multiphase chemistry - a review of microreactor design principles and reagent contacting modes , 2005 .

[19]  M. Marques.  Catalytic enantioselective cross-Mannich reaction of aldehydes. , 2006, Angewandte Chemie.

[20]  T. Opatz,et al.  Ring Contracting Rearrangements of 3‐Amino‐4‐(arylamino)‐1H‐isochromen‐1‐ones , 2006 .

[21]  Paul Watts,et al.  Green chemistry: synthesis in micro reactors , 2003 .

[22]  S. Haswell,et al.  The Application of Microreactor Technology for the Synthesis of 1,2-Azoles , 2004 .

[23]  Paul Watts,et al.  Micro reactors: principles and applications in organic synthesis , 2002 .

[24]  Rustem F Ismagilov,et al.  Multi-step synthesis of nanoparticles performed on millisecond time scale in a microfluidic droplet-based system. , 2004, Lab on a chip.

[25]  L. Angiolini,et al.  Further advances in the chemistry of mannich bases , 1990 .

[26]  K. Mae,et al.  Control of extremely fast competitive consecutive reactions using micromixing. Selective Friedel-Crafts aminoalkylation. , 2005, Journal of the American Chemical Society.

[27]  M. Greef,et al.  Recent Advances in Solution-Phase Multicomponent Methodology for the Synthesis of Heterocyclic Compounds , 2003 .

[28]  Peter H Seeberger,et al.  Microreactors as tools for synthetic chemists-the chemists' round-bottomed flask of the 21st century? , 2006, Chemistry.

[29]  Rustem F Ismagilov,et al.  Using microfluidics to observe the effect of mixing on nucleation of protein crystals. , 2005, Journal of the American Chemical Society.

[30]  Robin Fortt,et al.  Thermal optimisation of the Reimer-Tiemann reaction using thermochromic liquid crystals on a microfluidic reactor. , 2005, Lab on a chip.

[31]  Paul Watts,et al.  The application of micro reactors for organic synthesis. , 2005, Chemical Society reviews.

[32]  J. Burns,et al.  The intensification of rapid reactions in multiphase systems using slug flow in capillaries. , 2001, Lab on a chip.

[33]  Albert Renken,et al.  Microstructured reactors for catalytic reactions , 2005 .