Use of the ring opening reactions of 1,3,5-triazines in organic synthesis (review)

Abstract

Published data on the recyclization reactions of 1,3,5-triazines are reviewed. The classification is based on the fragments of the 1,3,5-triazine molecules used in the construction of new heterocycles.

Synthesis of 2-Azapyrenes and Their Photophysical and Electrochemical Properties

“…IR (ATM, cm −1 ): ṽ = 750 (vs), 822 (s), 892 (m), 1269 (w), 1399 (m), 1488 (m), 1597 (w), 1725 (w), 2207 (vw), 2852 (w), 2920 (w), 3023 (w). MS (EI, 70 eV): m/z = 370 (27), 369 (M + , 100), 368 (55), 354 (42), 352 (20), 176 (36), 162 (19), 77 (57), 51 (26). HRMS (EI) m/z: [M + ] calcd for C 28 H 19 N 369.1512, found 369.1500.…”

“…Mp: 119−121 °C. (32), 383 (M + , 100), 382 (53), 368 (36), 290 (13), 277 (12), 183 (31), 176 (28), 91 (27), 65 (23). HRMS (EI) m/z: [M + ] calcd for C 29 H 21 N 383.1669, found 383.1665.…”

“…Synthetic strategies for the construction of azapyrenes have been previously reported on the basis of multistep procedures with a set of drawbacks, e.g., harsh conditions, expensive or complex starting materials, low selectivity, and only low functionalization potential. − With regard to 2-azapyrenes (naphtho­[2,1,8- def ]­isoquinolines), only the unsubstituted parent compound has been reported in the literature so far. This compound has been prepared by thermal cyclization, by using a lengthy nine step-sequence, by PPA (polyphosphoric acid)-induced Beckmann rearrangement, and by peri -annulation with sym -triazines .…”

Syntheses and Structural Investigations of Penta-Coordinated Co(II) Complexes with Bis-Pyrazolo-S-Triazine Pincer Ligands, and Evaluation of Their Antimicrobial and Antioxidant Activities

“…s-Triazines are widely used within the pharmaceutical, textile, plastic, and rubber industries, and as pesticides, dyestuffs, optical bleaches, explosives, and surface-active agents [4][5][6]. s-Triazine and its compounds are also used as subunits in the formation of supramolecular structures because they possess good optical and electronic properties and are able to form three strong hydrogen bonds with the host molecule [7].…”

New one-pot reaction of perimidines with nitroethane and acylating agents in polyphosphoric acid

“…Similar processes involving 1,3,5 tri azines in PPA are considered in details in the review. 17 Compounds 4a-i undergo hydrolysis after treatment of the reaction mixture with water to give indoles 5a-i.…”