𝔖 Bobbio Scriptorium
✦   LIBER   ✦

A novel solid support for derivatization and subsequent N-alkylation of secondary amines: Preparation of N-alkylated 5- and 6-alkoxy-1,2,3,4-tetrahydroisoquinolines via mitsunobu reaction

✍ Scribed by Petri Heinonen; Harri Lönnberg

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
215 KB
Volume
38
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

A hydroxymethylated polystyrene resin has been convened to its vinyisuifonylethyl ether (1) by DBU catalyzed addition of the hydmxy groups to divinyl sulfone. The support obtained was used to convert 5-and 6-(tetrahydropyran-2-yloxy)-1,2,3,4-tetrahydroisoquinolines to a set of N-alkylated tetrahydroisoquinolines bearing various 5-and 6-alkoxy substituents (Sa-m). The synthesis involved attachment of the slatting material to the support by Michael addition, acid-catalyzed removal of the ~1 protection, Mitsunobu etherification, quaternarization with alkyl amines, and release in solution with diisopropylethylamine.

📜 SIMILAR VOLUMES

Reaction of metallo S-alkyl N-cyanodithi
Reaction of metallo S-alkyl N-cyanodithioiminocarbonates and alkyl N-cyanocarbamates with hydrazine. A novel preparation of 5-amino-3-mercapto-1,2,4-triazole
✍ Lyndon K. Marble; Wallace E. Puckett; William Russell Summers 📂 Article 📅 1998 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 496 KB

## Abstract Metal salts of __S__‐alkyl‐__N__‐cyanodithioiminocarbonates 7 react as __electrophiles__ with hydrazine hydrate to form 5‐amino‐3‐mercapto‐1__H__‐1,2,4‐triazole 1. The novel 4‐cyanothiosemicarbazide 9 is proposed as the intermediate which cyclizes to the aromatic triazole. The rate dete