Potential of alkyl orthoformates as alkylating agents of non‐electron rich nitrogen heterocycles

Abstract

Findings and suggestions about the potential of the alkyl orthoformates as alkylating agents of non electron rich nitrogen heterocycles and unambiguous instrumental and chemical characterization of the alkylated compounds are reported.

Synthesis and Dimroth Rearrangement of 6-Cyano-l,2,4-triazolo- [4,3-a]pyrimidin-5- and 7-ones. A Novel Alkylation with Orthoesters and a New Participation of the Cyano Group in the Rearrangement

“…It is identical with the p ro duct from m ethod a. 6 -C yan o-4-m eth y 1-2,5-d ip h en y 1-1,2,4-triazolo-[1 ,5-a] (30) A suspension of 4 [28] (0.48 g, 2.11 m m ol) in ethanol (10 m l) and benzaldehyde (1 m l) with 2 drops of acetic acid was h eated u n d er reflux for 1 h. D uring the reaction p eriod the hydrazine dis solved w ith the form ation of the hydrazone. The pro d u ct was filtered and crystallized from ethanol as yellow crystals (0.42 g, 60% yield); m.p.…”

Novel Quinazoline Derivatives Bearing a Sulfapyridine Moiety as Anticancer and Radiosensitizing Agents

“…Treatment of compound 4 with hydrazine hydrate in ethanol afforded the corresponding N‐amino derivative 5b . The formation of compound 5b was assumed to occur via elimination of 1 mol H 2 S of intermediate 5a followed by intramolecular cyclization to give the N‐amino derivative 5b (lead acetate paper). The IR spectrum of compound 5 showed bands at 3410, 3308, and 3183 cm −1 (NH, NH 2 ), 1660 cm −1 (C═O), and 1383 and 1133 cm −1 (SO 2 ).…”

Synthesis of some novel triazoloquinazolines and triazinoquinazolines and their evaluation for anti-inflammatory activity

“…Treatment of compounds 3 or 4 with hydrazine hydrate in ethanol afforded the corresponding N-amino derivatives 5 and 6 (Scheme 1). The formation of compounds 5 and 6 via the reaction of 3 or 4 with hydrazine hydrate was assumed to be via elimination of 1 mol H 2 S followed by intramolecular cyclization (Guccion et al, 1995) to give the N-amino derivatives 5, 6 (lead acetate paper). IR spectrum of compound 5 showed bands at 3350, 3300, 3250 (NH, NH 2 ), 1687 (C=O).…”