Catalytic Synthesis of 2H‐Chromenes

نویسندگان

  • Nilanjana Majumdar
  • Nanda D. Paul
  • Sutanuva Mandal
  • Bas de Bruin
  • William D. Wulff
چکیده

2H-Chromenes (2H-1-benzopyran derivatives) display a broad spectrum of biological activities. The 2H-chromene substructure is an important structural motif present in a variety of medicines, natural products, and materials showing unique photophysical properties. Hence, the structural importance of the benzopyran moiety has elicited a great deal of interest in the field of organic synthesis and chemical biology to develop new and improved synthesis of these molecular skeletons. This review gives an up-to-date overview of different catalytic methodologies developed for the synthesis of 2H-chromenes and is structured around the three main approaches applied in catalytic 2H-chromene synthesis: (I) catalysis with (transition) metals, (II) metal-free Brønsted and Lewis acid/base catalysis, which includes examples of nonenantioselective organocatalysis, and (III) enantioselective organo-catalysis. The section in which the metal-catalyzed reactions are discussed describes different ring-closing strategies based on (transition) metal catalysis, including a few enantioselective approaches. For most of these reactions, plausible mechanisms are delineated. Moreover, synthesis of some natural products and medicinally important drugs are included. Specific advantages and disadvantages of the several synthetic methodologies are discussed. The review focuses on catalytic 2H-chromene synthesis. However, for a complete overview, synthetic routes involving some stoichiometric steps and reactions producing ring-scaffolds that are closely related to 2Hchromenes are also included.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Catalytic enantioselective synthesis of 2-aryl-chromenes.

An enantioselective Pd-catalyzed 6-endo-trig reaction for the synthesis of 2-aryl-chromenes has been developed. A systematic optimization of a TADDOL-derived ligand set resulted in the identification of a novel monodentate phosphoramidite-palladium catalyst that accesses 2-aryl-2H-chromenes with high yield and enantioselectivity under mild conditions. The products obtained from this method can ...

متن کامل

Bi(OTf)3-catalyzed addition of isocyanides to 2H-chromene acetals: an efficient pathway for accessing 2-carboxamide-2H-chromenes.

Bismuth triflate (Bi(OTf)3) is identified as an efficient catalyst for the direct addition of isocyanides to 2H-chromene acetals. The large scope of isocyanides and chromene acetals makes them suitable substrates in this catalytic system. By this synthetic strategy, a polyfunctional molecular scaffold, 2-carboxamide-2H-chromenes could be prepared efficiently in one step up to 95% yield. In addi...

متن کامل

A practical way to synthesize chiral fluoro-containing polyhydro-2H-chromenes from monoterpenoids

Conditions enabling the single-step preparative synthesis of chiral 4-fluoropolyhydro-2H-chromenes in good yields through a reaction between monoterpenoid alcohols with para-menthane skeleton and aldehydes were developed for the first time. The BF3·Et2O/H2O system is used both as a catalyst and as a fluorine source. The reaction can involve aliphatic aldehydes as well as aromatic aldehydes cont...

متن کامل

One-pot pseudo-five-component synthesis of dihydropyrano[2,3-g] chromenes using sodium phthalimide/[BMIM]BF4 as high efficient catalytic system

An efficient route for the synthesis of dihydropyrano[2,3-g] chromenes via one-pot pseudo-five component cyclization reaction of an aldehyde, malononitrile and 2,5-dihydroxy-1,4-benzoquinone in the presence of an effective and mild catalytic system containing sodium phthalimide and 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM]BF4) ionic liquid (SPI/IL) was studied. The reacti...

متن کامل

One-pot pseudo-five-component synthesis of dihydropyrano[2,3-g] chromenes using sodium phthalimide/[BMIM]BF4 as high efficient catalytic system

An efficient route for the synthesis of dihydropyrano[2,3-g] chromenes via one-pot pseudo-five component cyclization reaction of an aldehyde, malononitrile and 2,5-dihydroxy-1,4-benzoquinone in the presence of an effective and mild catalytic system containing sodium phthalimide and 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM]BF4) ionic liquid (SPI/IL) was studied. The reacti...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره   شماره 

صفحات  -

تاریخ انتشار 2015