Abstract
Diversity-oriented organic synthesis (DOS) and solid-phase organic synthesis (SPOS) are proven technologies for generating small molecule libraries for chemical genetics studies. Integration of controlled microwave heating with DOS and SPOS not only speeds up the library preparation process but also offers unique opportunities in tackling issues which are hardly addressed by thermal heating. Microwave-assisted synthesis is illustrated for (a) highly regioselective Wittig olefination of cycloalkanones by accurate regulation of temperature; (b) tandem Wittig-IMDA sequence toward stereochemical diversity of γ-butyrolactones; (c) one-pot alkylation-amidation approach toward appendage diversity through use of building blocks; and (d) one-pot U-4CR-annulation strategy toward skeletal diversity via careful reaction design. Microwave-assisted solid-phase organic synthesis (MASPOS) is highlighted by incorporating with split-pool combinatorial synthesis (SPCS) of indole sulfonamides via a key on-resin Cu(II)- or Pd(II)-catalyzed heteroannulation under microwave heating. Design and fabrication of a novel diglycine-derived cat·linker are described and its role in facilitating on-resin reaction is evaluated. A traceless synthesis of indole sulfonamides via microwave-assisted Cu(II)- catalyzed heteroannulation of the cat·linker-tethered substrates is also given.
Keywords: Annulation, diversity-oriented synthesis, heterocycles, linker, microwave, multi-component reactions, solid-phase organic synthesis, tandem reactions
Combinatorial Chemistry & High Throughput Screening
Title: Diversity-Oriented Synthesis and Solid-Phase Organic Synthesis Under Controlled Microwave Heating
Volume: 10 Issue: 10
Author(s): Wei-Min Dai and Jianyu Shi
Affiliation:
Keywords: Annulation, diversity-oriented synthesis, heterocycles, linker, microwave, multi-component reactions, solid-phase organic synthesis, tandem reactions
Abstract: Diversity-oriented organic synthesis (DOS) and solid-phase organic synthesis (SPOS) are proven technologies for generating small molecule libraries for chemical genetics studies. Integration of controlled microwave heating with DOS and SPOS not only speeds up the library preparation process but also offers unique opportunities in tackling issues which are hardly addressed by thermal heating. Microwave-assisted synthesis is illustrated for (a) highly regioselective Wittig olefination of cycloalkanones by accurate regulation of temperature; (b) tandem Wittig-IMDA sequence toward stereochemical diversity of γ-butyrolactones; (c) one-pot alkylation-amidation approach toward appendage diversity through use of building blocks; and (d) one-pot U-4CR-annulation strategy toward skeletal diversity via careful reaction design. Microwave-assisted solid-phase organic synthesis (MASPOS) is highlighted by incorporating with split-pool combinatorial synthesis (SPCS) of indole sulfonamides via a key on-resin Cu(II)- or Pd(II)-catalyzed heteroannulation under microwave heating. Design and fabrication of a novel diglycine-derived cat·linker are described and its role in facilitating on-resin reaction is evaluated. A traceless synthesis of indole sulfonamides via microwave-assisted Cu(II)- catalyzed heteroannulation of the cat·linker-tethered substrates is also given.
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Cite this article as:
Dai Wei-Min and Shi Jianyu, Diversity-Oriented Synthesis and Solid-Phase Organic Synthesis Under Controlled Microwave Heating, Combinatorial Chemistry & High Throughput Screening 2007; 10 (10) . https://dx.doi.org/10.2174/138620707783220338
DOI https://dx.doi.org/10.2174/138620707783220338 |
Print ISSN 1386-2073 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5402 |
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