ChemInform Abstract: A Convenient Synthesis of 1,1-Disubstituted 1,2,3,4-Tetrahydroisoquinolines via Pictet-Spengler Reaction Using Titanium(IV) Isopropoxide and Acetic-Formic Anhydride

Autor:	Hirokazu Kodama, Takehiro Sano, Masayoshi Nakamura, Tsuyoshi Yoshimura, Yoshie Horiguchi, Toshiaki Saitoh, Hiroko Hamada, Kaori Hanezi
Rok vydání:	2010
Předmět:	chemistry.chemical_compound Pictet–Spengler reaction Chemistry Reagent Acetic formic anhydride Trifluoroacetic acid chemistry.chemical_element Organic chemistry General Medicine Titanium
Zdroj:	ChemInform. 33
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200230184
Popis:	A synthesis of 1,1-disubstituted 1,2,3,4-tetrahydroisoquinolines (6) was achieved in a highly efficient manner via Pictet-Spengler reaction of arylethylamines (1) and acyclic and cyclic ketones (2) using titanium (IV) isopropoxide and acetic-formic anhydride. The cyclization of the in situ formed acyliminium ion (4) to N-formyl 1,2,3,4-tetrahydroisoquinoline (5) was greatly facilitated by using trifluoroacetic acid as an additional reagent. The Pictet-Spengler reaction was carried out by one pot procedure, providing a convenient and effective method for preparing various 1,2,3,4-tetrahydroisoquinolines.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::29028198136699f8f3fa4ae3cfa1c156 https://doi.org/10.1002/chin.200230184 Zobrazit plný text záznamu Plný text