Solid-Supported Benzotriazoles:  Synthetic Auxiliaries and Traceless Linkers for the Combinatorial Synthesis of Amine Libraries

Abstract

This paper describes the successful transfer of benzotriazole-based chemistry on solid support. The strategy followed to anchor this peculiar heterocycle on solid phase and the full analytical characterization of the various supported benzotriazoles are herein described. The chemistry assessment process on solid phase, the preparation of discrete libraries by parallel synthesis, the semiautomated purification procedures, and the complete analytical characterization of the library components are also presented and discussed.

Palladium and half sandwich ruthenium(II) complexes of selenated and tellurated benzotriazoles: Synthesis, structural aspects and catalytic applications

“…They show biological activities [2,3]. Solid supported benzotriazoles have been used for combinatorial synthesis of amine libraries [4]. Their potential as UV stabilizers for polymers has also been reported [5].…”

“…for [RuCl(g 6 -p-cymene){2,3-bis(2-pyridyl)pyrazine}]ÁBF4 [50] and 2.077(3)À2.113(3) Å for Ru(II)(g 6 -p-cymene)-complexes of oxazoline-based ligands[51]. The Ru-Te bond length (2.6183(10) Å) of cation of 4 is consistent with earlier reports 2.619(8) Å for [RuCl 2 (g 6 -p-cymene)L] where L is 2-(4-ethoxyphenyl telluromethyl)tetrahydro-2H-pyran[52] and 2.6371(4) Å for [{RuCl(g 6 -p-cymene)(H 2 NCH 2 CH 2 TeC 6 H 4 OMe)ClÁH 2 O] [46].…”

Cysteinoyl‐ and Cysteine‐containing Dipeptidoylbenzotriazoles with Free Sulfhydryl Groups: Easy Access to N‐terminal and Internal Cysteine Peptides

“…Preparation of N-Cbz-, N-Boc-, and N-Fmoc-Lcysteines 4a-c The amino group of L-cysteine 2 has been selectively acylated using N-Cbz-1H-benzotriazole 1a (23,24), N-Boc-1H-benzotriazole 1b (25,26), and N-Fmoc-1H-benzotriazole 1c. According to our previously reported method (32), reactions of N-Cbz, N-Boc-, and N-Fmoc-1H-benzotriazoles 1a-c with L-cysteine 2 at 20°C in the presence of 2 equivalents of triethylamine in CH 3 CN-H 2 O (3:1) each gave selectively the corresponding N-protected, free sulfhydryl L-cysteines 2a-c (Scheme 1, Table 1) in yields of 70-75%.…”

“…1b was synthesized according to literature method (25,26). White microcrystals, yield 50%, mp 70.0–72.0 °C (lit., (25,26) 62.0–63.0 °C); 1 H NMR (CDCl 3 ) δ 8.22–8.02 (m, 2H), 7.64 (t, J = 7.8 Hz, 1H), 7.48 (t, J = 7.8 Hz, 1H), 1.77 (s, 9H); 13 C NMR (CDCl 3 ) δ 146.8, 146.1, 131.8, 130.0, 125.6, 120.4, 113.7, 87.1, 28.2.…”

“…(23,24) 1a was synthesized according to literature method. (23,24) White microcrystals, yield 85%, mp 108-110°C (lit., (23) N-Boc-1H-Benzotriazole (1b) (25,26) 1b was synthesized according to literature method (25,26). White microcrystals, yield 50%, mp 70.0-72.0°C (lit., (25,26)…”