Benzotriazol‐1‐ylmethylammonium salts synthesis and reactivity

Abstract

Benzotriazol‐1‐ylmethylamines on treatment with alkylating agents afford benzotriazol‐1‐ylmethylammoni‐um salts, also available from reactions of chloromethylbenzotriazole with tertiary amines. In deuterated solvents under basic conditions the methylene protons of these salts exchange with deuterium. At elevated temperatures, an alkyl group substituent migrated from the ammonium center to the benzotriazolyl N‐3. Reactions of the salts with Grignard reagents afforded various products arising from substitution of the ammonium moiety and/or from attack on the benzotriazolyl N‐3 or on the benzenoid ring.

All-in-One: Achieving Robust, Strongly Luminescent and Highly Dispersible Hybrid Materials by Combining Ionic and Coordinate Bonds in Molecular Crystals

“…Selected cationic organic ligands were prepared according to reported procedures with some modifications. − For Route I, alkylation was controlled in such a way that it took place at one of the two N atoms. For Route II, alkylation occurred at the aromatic N. For Route III, alkylation happened at the functional group of the ligand.…”

2‐(1‐Benzotriazolyl)pyridine: A Robust Bidentate Ligand for the Palladium‐Catalyzed CC (Suzuki, Heck, Fujiwara–Moritani, Sonogashira), CN and CS Coupling Reactions

“…Di(1 H ‐benzo[ d ][1,2,3]triazol‐1‐yl)methane (L3): 38 The product was obtained as white needles (DCM/ether); yield: 0.225 g (90%); mp 78–80 °C; 1 H NMR (300 MHz, CDCl 3 ): δ =8.06 (d, J =8.4 Hz, 1 H), 7.95 (d, J =8.4 Hz, 1 H), 7.87–7.83 (m, 2 H), 7.56 (dt, J =6.3 and 0.9 Hz, 1 H), 7.42–7.36 (m, 5 H); 13 C NMR (75 MHz, CDCl 3 ): δ =146.3, 145.0, 132.6, 128.6, 127.5, 124.6, 120.2, 118.5, 109.9, 64.8; HR‐MS (ESI): m/z =250.0965, calcd. for C 13 H 10 N 6 (M+H + ): 250.0967.…”

Study of the Orientation of Lithiation of 1- and 2-Alkylbenzotriazoles

“…a Defined in Experimental section. 6 The percentage of the compound in the reaction mixture, as measured by GC, is given in parentheses. c Lit.9 d Overall yield of 4-, 5(6)-, and 7-deuterated compounds.e Lit.1 (ppm); J (Hz); m = multiplicity: s = singlet, d = doublet, t = triplet, q = quartet, h = septet, m = multiple!…”

“…60, No. 5, 19951247 zotriazol-l-yl)-5-n-butyl-6,6-dimethyl-3-isopropyl-5-iodo-[2.2.2]bicyclooctadiene (9a) (1%), (vii) 2-(benzotriazol-lyl)-3-isopropyl-5,6,6-trimethyl[2.2.2]bicyclooctadiene (10) (13%), and (viii) 2,3-bis(benzotriazol-l-yl)-2,3-dimethylbutane (6)…”

“…C, 37.65 (37.78); , 3.51 (3.60); N,14.64 (14.37) C 67.48 (67.67); H 6.29(6.28); N 26.23 (26.39) -1: 292.142 (292.144)6 0 Oil (lit.6) 6. Mass weight calculated by the El + VE + LMR method.…”