Five-component synthesis of dihydropyridines based on diketene
Publish place: 20th Iranian Chemical Congress
Publish Year: 1397
نوع سند: مقاله کنفرانسی
زبان: English
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شناسه ملی سند علمی:
IRANCC20_563
تاریخ نمایه سازی: 28 اردیبهشت 1398
Abstract:
The 1,4-dihydropyridine (1,4-DHP) skeleton is one of the most versatile heterocyclic pharmacophores since it has been found as the central fragment in many clinical pharmaceuticals.[1] The most notable examples are the series of 1,4-DHP-based calcium channel blocker drugs such as nifedipine, felodipine, and nicardipine, which are still widely prescribed for the treatment of hypertension and related cardiovascular diseases.[1,2] In addition, the results obtained from a study with 1,4- DHPs as an a1aadrenoceptorselective antagonist discloses their promising potential in treating benign prostatic hyperplasia.[3] A novel five-component strategy involving commercially available diketene, primary amines, malononitrile and various benzaldehydes for the synthesis of densely functionalized 1,4-dihydropyridines in good yields was achieved. The reaction pathway involves a sequential ring-opening of diketene/enamine formation/Knoevenagel-condensation/Michael addition and 6-exo-tet cyclization,resulting in multiple bond-formation events including two C-C and three C-N bonds ultimately leading to the formation of the respective 1,4-dihydropyridines.
Authors
Atieh Rezvanian
Physics and Chemistry Faculty, Alzahra University, Tehran, Iran
Majid M. Heravi
Physics and Chemistry Faculty, Alzahra University, Tehran, Iran
Fahameh Mahmoodi
Physics and Chemistry Faculty, Alzahra University, Tehran, Iran
Zahra Shaabani
Physics and Chemistry Faculty, Alzahra University, Tehran, Iran