Synthesis of 1,2,3-triazoles containing an allomaltol moiety from substituted pyrano[2,3-d]isoxazolones via base-promoted Boulton–Katritzky rearrangement

• Constantine V. Milyutin,
• Andrey N. Komogortsev and
• Boris V. Lichitsky

Beilstein J. Org. Chem. 2024, 20, 1334–1340, doi:10.3762/bjoc.20.117

• terarylenes containing an allomaltol fragment were developed in our group [21][22][23][24][25][26]. Ongoing the research in this area, herein, we studied the reaction of aroyl containing substituted pyrano[2,3-d]isoxazolones 1 with various hydrazine hydrochlorides 2. It was shown that formed hydrazones 3

• undergo base-promoted Boulton–Katritzky rearrangement to appropriate 1,2,3-triazoles 4 (Scheme 1c). Based on the performed investigation a general approach to the preparation of corresponding terarylenes with a 3-hydroxy-4-pyranone unit was designed. Results and Discussion The starting ketones 1 were

Synthesis of substituted 8H-benzo[h]pyrano[2,3-f]quinazolin-8-ones via photochemical 6π-electrocyclization of pyrimidines containing an allomaltol fragment

• Constantine V. Milyutin,
• Andrey N. Komogortsev,
• Boris V. Lichitsky,
• Mikhail E. Minyaev and
• Valeriya G. Melekhina

Beilstein J. Org. Chem. 2023, 19, 778–788, doi:10.3762/bjoc.19.58

• [16][17][18][19][20]. The photochemical behavior of terarylenes containing an allomaltol fragment deserves special attention. In this case, two types of photoprocesses are possible: a 6π-electrocyclization of the 1,3,5-hexatriene system and the aforementioned ESIPT-induced transformation to α-hydroxy

• as a result of ESIPT-induced reactions (Scheme 1A and B). At the same time, both directions of phototransformation are realized for terarylenes with furan, pyrrole, and oxazolone-bridge fragments (Scheme 1C). However, the suppression of the ESIPT process in such systems makes it possible to perform

• the 6π-electrocyclization leading to polyaromatic products. Therefore, it is complicate to predict the photochemical behavior of terarylenes containing a 3-hydroxypyran-4-one unit. It should be noted that all the products considered above were constructed on the basis of five-membered heterocyclic

A study of the photochemical behavior of terarylenes containing allomaltol and pyrazole fragments

• Constantine V. Milyutin,
• Andrey N. Komogortsev,
• Boris V. Lichitsky and
• Valeriya G. Melekhina

Beilstein J. Org. Chem. 2022, 18, 588–596, doi:10.3762/bjoc.18.61

• -pyranone containing terarylenes with a pyrazole bridge fragment were studied. It was shown that UV-induced 6π-electrocyclization of the 1,3,5-hexatriene system was not observed for the considered objects molecules. At the same time, the phototransformation of such systems proceeds exclusively in the

• established by X-ray diffraction. Keywords: allomaltol; ESIPT process; photochemistry; pyrazoles; terarylenes; Introduction The investigation of the photochemical behavior of organic products is a significant part of modern materials science and technology. The UV-induced processes are extensively employed

• processes used in organic synthesis, 6π-electrocyclization of 1,3,5-hexatriene systems is attracting considerable attention [10][11][12][13][14][15][16][17]. The photocyclization of terarylenes leading to the formation of polyheterocyclic compounds is one of the most widely studied processes of this type

Click chemistry towards thermally reversible photochromic 4,5-bisthiazolyl-1,2,3-triazoles

• Chenxia Zhang,
• Kaori Morinaka,
• Mahmut Kose,
• Takashi Ubukata and
• Yasushi Yokoyama

Beilstein J. Org. Chem. 2019, 15, 2161–2169, doi:10.3762/bjoc.15.213

• thus prepared, which belong to the terarylene family, showed thermally reversible photochromism. The absorption maximum wavelengths of the closed forms are longer than other terarylenes reported so far. The thermal back reactions are much faster when the substituents on the terminal phenyl groups are

• large [6]; (3) when the substituent groups on the ring-closing carbon atoms are strongly electron-withdrawing [7]; or (4) when the dialkylamino group on the side chain [8] or a carbon atom of the conjugation system in a strained closed form [9] are protonated. Terarylenes [10][11], one of the closely

• photochromic diarylethenes containing triazole groups have been reported [20][21][22][23][24][25][26][27][28][29][30][31], all of them use the triazole ring as the linker of the second functional molecule with the diarylethene core. To the best of our knowledge, no diarylethenes or terarylenes possessing the