Parallel synthesis of 2-alkoxy and 2-acyloxyphenylpropyl amides and amines using dihydrocoumarins as versatile synthons. Application of a novel resin quench-capture method

The Combinatorial Synthesis of Bicyclic Privileged Structures or Privileged Substructures

“…A report by Bussolari et al also described a parallel synthesis of a small library in which a substituted coumarin ring was also the starting material. In the latter case, the coumarin ring was broken down to form a substituted benzene library …”

Improved one-pot synthesis of N, N-diisopropyl-3-(2-Hydroxy-5-methylphenyl)-3-phenyl propanamide; a key intermediate for the preparation of racemic Tolterodine

“…Ring opening reactions of dihydrocoumarins are well known in literature [9][10][11]. But in the present invention, we have described a new methodology (Scheme 1 & Scheme 2) for the preparation of N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamide (4) by using inexpensive and commercially vailable starting materials like 3, 4-dihydro-6-methyl 4-phenylcoumarin (2), which was synthesized from p-cresol and trans-cinnamic acid [12].…”

“…Based on the results, we observed the yield of compound 4 was increased to 75%, when 4 mole equivalents of acetic acid was used. But our attempts to increase the yield of compound 4 further by adding more equivalents of acetic [4][5][6][7][8][9][10][11][12]. Compounds 4a-4c and 5-5c are novel.…”

“…Compounds 4a-4c and 5-5c are novel. These compounds upon reduction [4][5][6][7][8][9][10][11][12] with LiAlH 4 , Vitride, Sodium borohydride gives corresponding amines, which are useful in the synthesis of Tolterodine and its related compounds.…”

Functionalised Polymers in Organic Chemistry; Part 2

“…A dual scavenger approach was developed by Bussolari for the synthesis of libraries of 2-alkoxy and 2-acyloxyphenylpropionamides and amines. 108 The general synthetic route is outlined in Scheme 45. Dihydrocoumarins were ring opened with a series of secondary amines, and subsequent phenol alkylation was performed.…”