Аннотация:
High temperature coupling of 6-aryl-5-cyano-3-(pyridin-2-yl)-1,2,4-triazines with 2-amino-4-aryloxazoles proceeds as the inverse demand Diels–Alder reaction between the oxazole moiety as dienophile and the 1,2,4-triazine moiety as diene to construct new 4,5-diaryl-6-cyano-3-hydroxypyridin-2-yl fragment. A reaction mechanism is proposed, and the structure of the key-product is proved by the X-ray diffraction analysis.
Образец цитирования:
A. P. Krinochkin, G. M. Reddy, D. S. Kopchuk, P. A. Slepukhin, Ya. K. Shtaitz, I. A. Khalymbadzha, I. S. Kovalev, G. A. Kim, I. N. Ganebnykh, G. V. Zyryanov, O. N. Chupakhin, V. N. Charushin, “2-Aminooxazoles as novel dienophiles in the inverse demand Diels–Alder reaction with 1,2,4-triazines”, Mendeleev Commun., 31:4 (2021), 542–544
Образцы ссылок на эту страницу:
https://www.mathnet.ru/rus/mendc983
https://www.mathnet.ru/rus/mendc/v31/i4/p542
Эта публикация цитируется в следующих 26 статьяx:
S. E. Vatolina, A. P. Krinochkin, A. A. Yurtaeva, A. S. Alekseeva, A. S. Markina, M. I. Valieva, V. V. Nadtochiy, O. V. Shabunina, D. S. Kopchuk, G. V. Zyryanov, “Reactions of 1,2-Diones with 3-Aminopyridine”, Russ J Gen Chem, 94:9 (2024), 2243
A. Rammohan, E. D. Ladin, Ya. K. Shtaitz, A. P. Krinochkin, I. A. Khalymbadzha, P. A. Slepukhin, D. S. Kopchuk, G. V. Zyryanov, V. N. Charushin, V. Ch. Ranu, “A New Approach to the Synthesis of [1,2,4]Triazolo[1,5-a]pyrimidines by Reaction of 1,2,4,5-Tetrazines with 2-Aminoxazoles”, Žurnal obŝej himii, 94:2 (2024), 209
A. Rammohan, A. P. Krinochkin, Yu. M. Sayfutdinova, Y. K. Shtaitz, S. S. Potapova, P. A. Slepukhin, V. S. Gaviko, D. S. Kopchuk, G. V. Zyryanov, O. N. Chupakhin, “Reaction of 6Н-5-(4-Fluorophenyl)-3-(2-pyridyl)-1,2,4-triazine with 4,5-Difluoro-1,2-dehydrobenzene”, Russ J Gen Chem, 94:9 (2024), 2255
I. I. Stoikov, I. S. Antipin, V. A. Burilov, A. R. Kurbangalieva, N. V. Rostovskii, A. S. Pankova, I. A. Balova, Yu. O. Remizov, L. M. Pevzner, M. L. Petrov, A. V. Vasilyev, A. D. Averin, I. P. Beletskaya, V. G. Nenajdenko, E. K. Beloglazkina, S. P. Gromov, S. S. Karlov, T. V. Magdesieva, A. A. Prishchenko, S. V. Popkov, A. O. Terent'ev, G. V. Tsaplin, T. P. Kustova, L. B. Kochetova, N. A. Magdalinova, E. A. Krasnokutskaya, A. V. Nyuchev, Yu. L. Kuznetsova, A. Yu. Fedorov, A. Yu. Egorova, V. S. Grinev, V. V. Sorokin, K. L. Ovchinnikov, E. R. Kofanov, A. V. Kolobov, V. L. Rusinov, G. V. Zyryanov, E. V. Nosov, V. A. Bakulev, N. P. Belskaya, T. V. Berezkina, D. L. Obydennov, V. Ya. Sosnovskikh, S. G. Bakhtin, O. V. Baranova, V. S. Doroshkevich, G. Z. Raskildina, R. M. Sultanova, S. S. Zlotskii, V. D. Dyachenko, I. V. Dyachenko, A. S. Fisyuk, V. V. Konshin, V. V. Dotsenko, E. A. Ivleva, A. N. Reznikov, Yu. N. Klimochkin, D. A. Aksenov, N. A. Aksenov, A. V. Aksenov, V. V. Burmistrov,, “Organic Chemistry in Russian Universities. Achievements of Recent Years”, Russ J Org Chem, 60:8 (2024), 1361
I. I. Stoykov, I. S. Antipin, V. A. Burilov, A. R. Kurbangalieva, N. V. Rostovsky, A. S. Pankova, I. A. Balova, Yu. O. Remizov, L. M. Pevzner, M. L. Petrov, A. V. Vasily, A. D. Averin, I. P. Beletskaya, V. G. Nenaydenko, E. K. Beloglazkina, S. P. Gromov, S. S. Karlov, T. V. Magdesieva, A. A. Prishchenko, S. V. Popkov, A. O. Terentyev, G. V. Tsaplin, T. P. Kustova, L. B. Kochetova, N. A. Magdalinova, E. A. Krasnokutskaya, A. V. Nyuchev, Yu. L. Kuznetsova, A. Yu. Fedorov, A. Yu. Egorova, V. S. Grinev, V. V. Sorokin, K. L. Ovchinnikov, E. R. Kofanov, A. V. Kolobov, V. L. Rusinov, G. V. Zyryanov, E. V. Nosov, V. A. Bakulev, N. P. Belskaya, T. V. Berezkina, D. L. Obydennov, V. Ya. Sosnovskikh, S. G. Bakhtin, O. V. Baranova, V. S. Doroshkevich, G. Z. Raskildina, R. M. Sultanova, S. S. Zlotskiy, V. D. Dyachenko, I. V. Dyachenko, A. S. Fisyuk, V. V. Konshin, V. V. Dotsenko, E. A. Ivleva, A. N. Reznikov, Yu. N. Klimochkin, D. A. Aksenov, N. A. Aksenov, A. V. Aksenov, V. V. Burmistrov, G. M. But, “Organic Chemistry in Russian Universities: Achievements of recent years”, Žurnal organičeskoj himii, 60:2-3 (2024)
A. Rammohan, A. P. Krinochkin, D. S. Kopchuk, Ya. K. Shtaitz, E. R. Sharafieva, V. S. Gaviko, G. V. Zyryanov, O. N. Chupakhin, “Reaction of 3-(Pyridin-2-yl)-1,2,4-triazine-5-carbonitriles with 2-Amino-4-aryl-1,3-oxazoles in Anhydrous Medium”, Russ J Org Chem, 59:9 (2023), 1633
A. P. Krinochkin, A. Rammohan, Ya. K. Shtaitz, D. S. Kopchuk, E. D. Ladin, E. R. Sharafieva, O. S. Taniya, G. V. Zyryanov, A. I. Matern, O. N. Chupakhin, “Interaction of 2-Amino-(4-aryl)-Substituted Thia- and Oxazoles with 5-Cyano-1,2,4-triazines”, Dokl Chem, 508:1 (2023), 28
P. A. Slepukhin, A. V. Rybakova, V. S. Gaviko, A. Rammohan, Ya. K. Shtaitz, A. P. Krinochkin, E. D. Ladin, D. S. Kopchuk, G. V. Zyryanov, V. L. Rusinov, “Single-crystal X-ray diffraction study of 4,5-diaryl-3-hydroxy-2,2′-bipyridine-6-carbonitriles”, Russ Chem Bull, 72:12 (2023), 2825
A. Rammohan, Ya. K. Shtaitz, E. D. Ladin, A. P. Krinochkin, P. A. Slepukhin, V. V. Sharutin, E. R. Sharafieva, T. A. Pospelova, D. S. Kopchuk, G. V. Zyryanov, “Solvent-Free Reaction of 3,6-Diaryl-1,2,4-triazine-5-carbonitriles with 2-Amino-4-aryloxazoles”, Russ J Gen Chem, 93:2 (2023), 263
Yaroslav K. Shtaitz, Aluru Rammohan, Alexey P. Krinochkin, Evgeny D. Ladin, Ilya I. Butorin, Nataliya N. Mochulskaya, Igor A. Khalymbadzha, Pavel A. Slepukhin, Vadim A. Shevyrin, Dmitry S. Kopchuk, Grigory V. Zyryanov, Oleg N. Chupakhin, “Highly Regioselective Synthesis of 3,6‐Diaryl‐2‐(het)arylpyridines by aza‐Diels‐Alder Reactions between 6‐H‐1,2,4‐Triazine Dienes and 2‐Amino‐4‐aryloxazole‐Based Dienophiles”, ChemistrySelect, 8:26 (2023)
Aluru Rammohan, A. P Krinochkin, D. S Kopchuk, Ya. K Shtaitz, E. R Sharafieva, V. S Gaviko, G. V Zyryanov, O. N Chupakhin, “Interaction of 3-(2-pyridyl)-1,2,4-triazine-5-carbonitriles with 2-amino-4-aryloxazoles in the absence of water”, Žurnal organičeskoj himii, 59:9 (2023), 1233
A. P. Krinochkin, A. Rammohan, Ya. K. Shtaitz, D. S. Kopchuk, E. D. Ladin, E. R. Sharafieva, O. S. Taniya, G. V. Zyryanov, A. I. Matern, O. N. Chupakhin, “INTERACTION OF 2-AMINO-(4-ARYL)-SUBSTITUTED THIA- AND OXAZOLES WITH 5-CYANO-1,2,4-TRIAZINES”, Doklady Rossijskoj akademii nauk. Himiâ, nauki o materialah., 508:1 (2023), 55
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R. Alan Aitken, Fiona M. Fotherby, Progress in Heterocyclic Chemistry, 34, 2023, 469
M. I Valieva, A. Rammohan, E. S Starnovskaya, E. A Kudryashova, A. P Krinochkin, D. S Kopchuk, G. V Zyryanov, O. N Chupakhin, “Reactions of 5-(1,2-dicarbadodecaboran-1-yl)-3-(2-pyridyl)1,2,4-triazines with dienophiles”, Žurnal obŝej himii, 93:3 (2023), 379
A. Rammohan, Ya. K. Shtaitz, E. D Ladin, A. P Krinochkin, P. A Slepukhin, V. V Sharutin, E. R Sharafieva, T. A Pospelova, D. S Kopchuk, G. V. Zyryanov, “Solvent-Free reaction of 3,6-Diaryl-1,2,4-Triazine-5-Carbonitriles with 2-Amino-4-aryloxazoles”, Žurnal obŝej himii, 93:2 (2023), 200
Aluru Rammohan, Alexey P. Krinochkin, Albert F. Khasanov, Dmitry S. Kopchuk, Grigory V. Zyryanov, “Sustainable Solvent-Free Diels–Alder Approaches in the Development of Constructive Heterocycles and Functionalized Materials: A Review”, Top Curr Chem (Z), 380:5 (2022)
P. A. Slepukhin, A. P. Krinochkin, E. S. Starnovskaya, Ya. K. Shtaitz, M. I. Savchuk, D. S. Kopchuk, I. N. Egorov, S. Santra, G. V. Zyryanov, O. N. Chupakhin, “Single-crystal X-ray diffraction analysis of arylamine-containing 2,2′-bipyridine derivatives”, Russ Chem Bull, 71:7 (2022), 1533
Nikita S. Mayorov, Mikhail Yu. Ievlev, “Modern Methods for the Synthesis of Cyano-Substituted Bipyridine Derivatives (microreview)”, Chem Heterocycl Comp, 58:6-7 (2022), 301
A. P. Krinochkin, M. I. Valieva, E. S. Starnovskaya, Ya. K. Shtaitz, S. S. Rybakova, E. R. Sharafieva, D. S. Kopchuk, G. V. Zyryanov, V. L. Rusinov, “The Synthetic Approaches to (3-Thienyl)-Containing 2,2'-Bipyridines as Potential Monomers for Electropolymerization”, Dokl Chem, 506:1 (2022), 196
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