Reaction of phosgene with the tricycle related to the minor base of phenylalanine transfer ribonucleic acids.
1-Benzylwye (8) underwent electrophilic substitution at the 7-position in the presence of phosgene and pyridine in tetrahydrofuran (THF) to afford the 1,4-dihydropyridines (11, 10, and 14) together with the carboxylic acid 6 and its methyl ester 2 after short treatment of the reaction mixture with methanol and then with water. When triethylamine was used instead of pyridine, phosgene reacted with triethylamine rather than 8, producing (E)-3-(diethylamino)propenoyl chloride (17) and diethylcarbamoyl chloride (18).
Itaya
Taisuke
T
Faculty of Pharmaceutical Sciences, Kanazawa University, Kanazawa, Japan. itaya@mail.p.kanazawa-u.ac.jp
Kanai
Tae
T
D001593:Benzyl Compounds / Q000737:chemistry*; D005021:Ethylamines / Q000737:chemistry; D010705:Phosgene / Q000737:chemistry*; D011687:Purines / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D012360:RNA, Transfer, Phe / Q000138:chemical synthesis*
C474054:1-benzylwye; D001593:Benzyl Compounds; D005021:Ethylamines; D011687:Purines; D011725:Pyridines; D012360:RNA, Transfer, Phe; D010705:Phosgene; C023666:pyridine; C016162:triethylamine