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Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Review Article

Construction of Versatile N-Heterocycles from in situ Generated 1,2-Diaza-1,3-dienes

Author(s): Zhangpei Chen*, Lingxin Meng, Zhiqiang Ding and Jianshe Hu*

Volume 23, Issue 2, 2019

Page: [164 - 187] Pages: 24

DOI: 10.2174/1385272823666190227162840

Price: $65

Abstract

N-Heterocyclic architectures are omnipresent in many bioactive natural products, synthetic drugs, and materials science, thus have evoked a vast research interest of academic, as well as industrial chemists. Recently, several efficient methods have been developed for the preparation of various nitrogen-containing compounds with in situ generated 1,2-diaza-1,3-dienes from the easily available precursors including α -haloketohydrazones, α-hydroxyl ketohydrazones, thiadiazole dioxides or their analogues, and other simple hydrazones. These methods are considered powerful tools in the synthesis of five-, six- and seven-membered ring heterocyclic compounds with good to excellent levels of conversions and selectivities. This review mainly summarizes recent advances on the chemistry of construction of versatile N-heterocycles from in situ generated 1,2-diaza-1,3- dienes and presents an extensive summary of the application scopes and limitations of the corresponding cyclization reactions. Moreover, enantioselective approaches are also covered.

Keywords: 1, 2-Diaza-1, 3-dienes, azoalkanes, N-Heterocycles, cyclization reactions, annulations, Aza-Diels-Alder reaction.

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[1]
(a)Kobayashi, J.; Morita, H. In: The Alkaloids. Vol. 60; Cordell, G.A., Ed.; Academic Press: New York, 2003; pp. 165-210.
(b)Joule, J.A.; Mills, K. In Heterocyclic Chemistry, 5th ed; John Wiley & Sons, 2010, pp. 97-100.
(c) Eftekhari-Sis, B.; Zirak, M.; Akbari, A.; Hashemi, M.M. Synthesis of new 2-aryl-4-chloro-3-hydroxy-1h-indole-5,7-dicarbaldehydes via vilsmeier-haack reaction. J. Heterocycl. Chem., 2010, 47, 463-467.
(d) Eftekhari-Sis, B.; Akbari, A.; Amirabedi, M. Synthesis of new n-alkyl(aryl)-2,4-diaryl-1h-pyrrol-3-ols via aldol paal-knorr reactions. Chem. Heterocyclic Com+., 2011, 46, 1330-1334.
(e) Eftekhari-Sis, B.; Zirak, M.; Akbari, A. Arylglyoxals in synthesis of heterocyclic compounds. Chem. Rev., 2013, 113, 2958-3043.
[2]
(a) Majumdar, K.C.; Roy, B.; Debnath, P.; Taher, A. Metal-mediated heterocyclization: synthesis of heterocyclic compounds containing more than one heteroatom through carbon-heteroatom bond forming reactions. Curr. Org. Chem., 2010, 14, 846-887.
(b) Chen, Z-P.; Zhou, Y-G. Asymmetric hydrogenation of heteroarenes with multiple heteroatoms. Synthesis, 2016, 48, 1769-1781.
[3]
(a) Attanasi, O.A.; De Crescentini, L.; Favi, G.; Filippone, P.; Mantellini, F.; Perrulli, F.R.; Santeusanio, S. Cultivating the passion to build heterocycles from 1,2-diaza-1,3-dienes: the force of imagination. Eur. J. Org. Chem., 2009, 2009, 3109-3127.
(b) Lemos, A. Addition and cycloaddition reactions of phosphinyl- and phosphonyl-2H-azirines, nitrosoalkenes and azoalkenes. Molecules, 2009, 14, 4098-4119.
(c) Attanasi, O.A.; De Crescentini, L.; Filippone, P.; Mantellini, F.; Santeusanio, S. 1,2-Diaza-1,3-butadienes: just a nice class of compounds, or powerful tools in organic chemistry? Reviewing an experience. Arkivoc, 2002, 2002, 274-292.
(d) Attanasi, O.A.; Filippone, P. Working twenty years on conjugated azo-alkenes (and environs) to find new entries in organic synthesis. Synlett, 1997, 1997, 1128-1140.
[4]
(a) Attanasi, O.A.; Grossi, M.; Mei, A.; Serra-Zanetti, F. Synthesis of unusual conjugated azoalkenes. Org. Prep. Proced. Int., 1988, 20, 408-414.
(b) Attanasi, O.; Filippone, P.; Mei, A.; Serra-Zanetti, F. Conjugated azoalkenes. Part II. Synthesis of some heterocyclic azoalkenes. J. Heterocycl. Chem., 1985, 22, 1341-1343.
[5]
Selected examples on the synthesis of N-heterocycles via isolated DDs, see:(a) Shao, J.; Chen, W.; Zhao, M.; Shu, K.; Liu, H.; Tang, P. Substratecontrolled synthesis of spirocyclopropylpyrazolones and bicyclic 4,5- dihydropyrazoles from 1,2-diaza-1,3-dienes with sulfur ylides.. Org. Lett.., 2018, 20, 3992-3995.
(b) Zhao, , M.; Li, , X.; Shao,, J.; Chen,, W. Xie, N.; Yuan, H.; Sun, Q.; Zhang, W. Synthesis of pyrimidopyrrolopyridazines via a tandem reaction of heterocyclic ketene aminals with 1,2-diaza-1,3-dienes. Org. Lett., 2018, 20, 3057-3060.
(c) Santeusanio, S.; Majer, R.; Perrulli, F.R..; Crescentini, L. De, Favi G.; Giorgi, G.; Mantellini, F. Divergent approach to thiazolylidene derivatives: a perspective on the synthesis of a heterocyclic skeleton from β-amidothioamides reactivity. J. Org. Chem.., 2017, 82, 9773-9778.
(d) Ran, , G.-Y.; Gong, , M.; Yue, , J.-F.; Yang,, X.-X. Zhou, S.-L.; Du, W.; Chen, Y.-C. Asymmetric cascade assembly of 1,2-diaza-1,3-dienes and α, β-unsaturated aldehydes via dienamine activation. Org. Lett., 2017, 19, 1874-1877.
(e) Mantenuto , S.; Cayuelas, A..; Favi , G.; Attanasi, O.A. Mantellini, F.; Nájera, C.; Sansano, J.M. Reactivity of 1,2-diaza-1,3-dienes with azomethine ylides: [3+4] versus [3+2] cycloadditions. Eur. J. Org. Chem.., 2016, 4144-4151.
[6]
Boeckman, R.K., Jr; Ge, P.; Reed, J.E. New heterocyclic precursors for thermal generation of reactive, electron-rich 1,2-diaza-1,3-butadienes. Org. Lett., 2001, 3, 3647-3650.
[7]
Yang, H-T.; Wang, G-W.; Xu, Y.; Huang, J-C. Heterocycloaddition of thermally generated 1,2-diaza-1,3-butadienes to [60] fullerene. Tetrahedron Lett., 2006, 47, 4129-4131.
[8]
Al-Awadi, N.A.; Ibrahim, Y.A.; John, E.; Parveen, A. Pyrolysis of 3-hydroxy-2-arylhydrazonoalkanoic acid derivatives. Tetrahedron, 2011, 67, 1298-1307.
[9]
Lopes, S.M.M.; Brigas, A.F.; Palacios, F.; Lemos, A.; Pinho e Melo, T.M.V.D. [4+2] Cycloadditions of 3-tetrazolyl-1,2-diaza-1,3-butadienes: synthesis of 3-tetrazolyl-1,4,5,6-tetrahydropyridazines. Eur. J. Org. Chem., 2012, 2012, 2152-2160.
[10]
Attanasi, O.A.; Favi, G.; Mantellini, F.; Mantenuto, S.; Moscatelli, G.; Nicolini, S. Regioselective formation of 5-methylene-6-methoxy-1,4,5,6-tetrahydropyridazines from the [4+2]-cycloaddition reaction of in situ generated 1,2-diaza-1,3-dienes with methoxyallene. Synlett, 2015, 26, 193-196.
[11]
Deng, Y.; Pei, C.; Arman, H.; Dong, K.; Xu, X.; Doyle, M.P. Syntheses of tetrahydropyridazine and tetrahydro-1,2-diazepine scaffolds through cycloaddition reactions of azoalkenes with enol diazoacetates. Org. Lett., 2016, 18, 5884-5887.
[12]
Huang, R.; Tao, H-Y.; Wang, C-J. PPh3-mediated [4+2]- and [4+1]-annulations of maleimides with azoalkenes: access to fused tetrahydropyridazine/pyrrolidinedione and spiro-dihydropyrazole/ pyrrolidinedione derivatives. Org. Lett., 2017, 19, 1176-1179.
[13]
Zhang, Z.; Zhang, L.; Chen, Q.; Lu, T.; Zhou, Q. Synthesis of functionalized tetrahydropyridazines via catalyst-free self [4 + 2] cycloaddition of in situ generated 1,2-diaza-1,3-dienes. RSC Adv, 2016, 6, 61680-61685.
[14]
Shelke, A.M.; Suryavanshi, G. Fluoride-assisted synthesis of 1,4,5,6-tetrahydropyridazines via [4+2] cyclodimerization of in situ-generated azoalkenes followed by a C−N bond cleavage. Org. Lett., 2016, 18, 3968-3971.
[15]
Zhong, X.; Lv, J.; Luo, S. [4+2] Cycloaddition of in situ generated 1,2-diaza-1,3-dienes with simple olefins: facile approaches to tetrahydropyridazines. Org. Lett., 2015, 17, 1561-1564.
[16]
Zhong, X.; Lv, J.; Luo, S. Oxidative radical addition-cyclization of sulfonyl hydrazones with simple olefins by binary acid catalysis. Org. Lett., 2016, 18, 3150-3153.
[17]
Yang, X-L.; Peng, X-X.; Chen, F.; Han, B. TEMPO-mediated aza-Diels-Alder reaction: synthesis of tetrahydropyridazines using ketohydrazones and olefins. Org. Lett., 2016, 18, 2070-2073.
[18]
Zhao, H-W.; Pang, H-L.; Li, B.; Tian, T.; Chen, X-Q.; Song, X-Q.; Meng, W.; Yang, Z.; Liu, Y-Y.; Zhao, Y-D. Direct access to non-aromatic 1,2,3,6-tetrahydro-1,2,3,4-tetrazines via [4 + 2] cycloaddition of ahalogeno hydrazones with azodicarboxylic acid derivatives. RSC Adv, 2016, 6, 25562-25567.
[19]
Suo, Y.; Xie, M.; Chen, Y.; Zhang, Y.; Guo, Z.; Li, J.; Qu, G.; Guo, H. Synthesis of 1,2,3,4-Tetrazine derivatives via [4+2] cycloaddition of α-halo-N-acylhydrazones with diazodicarboxylates. Chin. J. Org. Chem., 2016, 36, 540-546.
[20]
Zhao, H-W.; Pang, H-L.; Zhao, Y-D.; Liu, Y-Y.; Zhao, L-J.; Chen, X-Q.; Song, X-Q.; Feng, N-N.; Du, J. Construction of 2,3,4,5-tetrahydro-1,2,4-triazines via [4+2] cycloaddition of α-halogeno hydrazones to imines. RSC Adv, 2017, 7, 9264-9271.
[21]
(a) Fang, X.; Zhang, J.W.; Wang, C.J. Asymmetric cycloaddition and cascade addition-cyclization reactions. In: Progress in enantioselective Cu(I)- catalyzed formation of stereogenic centers, Harutyunyan S. (eds); Springer, Cham. Top. Organomet. Chem; , 2015; 58, pp. 183-205.
(b) Chen, J-R.; Hu, X-Q.; Lu, L-Q.; Xiao, W-J. Formal [4+1] annulation reactions in the synthesis of carbocyclic and heterocyclic systems. Chem. Rev., 2015, 115, 5301-5365.
[22]
Gao, S.; Chen, J-R.; Hu, X-Q.; Cheng, H-G.; Lu, L-Q.; Xiao, W-J. Copper-catalyzed enantioselective inverse electron-demand hetero-Diels–Alder reactions of diazadienes with enol ethers: efficient synthesis of chiral pyridazines. Adv. Synth. Catal., 2013, 355, 3539-3544.
[23]
Wei, L.; Wang, C-J. The catalytic asymmetric synthesis of tetrahydropyridazines via inverse electron-demand aza-Diels-Alder reaction of enol ethers with azoalkenes. Chem. Commun., 2015, 51, 15374-15377.
[24]
Tong, M-C.; Chen, X.; Li, J.; Huang, R.; Tao, H.; Wang, C-J. Catalytic asymmetric synthesis of [2,3]-fused indoline heterocycles through inverse-electron-demand Aza-Diels–Alder reaction of indoles with azoalkenes. Angew. Chem. Int. Ed., 2014, 53, 4680-4684.
[25]
Li, J.; Huang, R.; Xing, Y-K.; Qiu, G.; Tao, H-Y.; Wang, C-J. Catalytic asymmetric cascade vinylogous Mukaiyama 1,6-Michael/Michael addition of 2-silyloxyfurans with azoalkenes: direct approach to fused butyrolactones. J. Am. Chem. Soc., 2015, 137, 10124-10127.
[26]
Huang, R.; Chang, X.; Li, J.; Wang, C-J. Cu(I)-catalyzed asymmetric multicomponent cascade inverse electron-demand aza-Diels-Alder/nucleophilic addition/ring-opening reaction involving 2-methoxyfurans as efficient dienophiles. J. Am. Chem. Soc., 2016, 138, 3998-4001.
[27]
Wei, L.; Zhu, Q.; Song, Z-M.; Liu, K.; Wang, C-J. Catalytic asymmetric inverse electron demand Diels-Alder reaction of fulvenes with azoalkenes. Chem. Commun., 2018, 54, 2506-2509.
[28]
Zhang, Z-J.; Song, J. An isothiourea-catalyzed asymmetric formal [4+2] cycloaddition of in situ generated azoalkenes with C1 ammonium enolates. Org. Chem. Front., 2018, 5, 2578-2582.
[29]
Boeckman, R.K., Jr; Reed, J.E.; Ge, P. A novel route to 2,3-pyrazol-1(5H)-ones via palladium-catalyzed carbonylation of 1,2-diaza-1,3-butadienes. Org. Lett., 2011, 3, 3651-3653.
[30]
Guo, C.; Sahoo, B.; Daniliuc, C.G.; Glorius, F. N-heterocyclic carbene catalyzed switchable reactions of enals with azoalkenes: formal [4+3] and [4+1] annulations for the synthesis of 1,2-diazepines and pyrazoles. J. Am. Chem. Soc., 2014, 136, 17402-17405.
[31]
Chen, J-R.; Dong, W-R.; Candy, M.; Pan, F-F.; Jörres, M.; Bolm, C. Enantioselective synthesis of dihydropyrazoles by formal [4+1] cycloaddition of in situ-derived azoalkenes and sulfur ylides. J. Am. Chem. Soc., 2012, 134, 6924-6927.
[32]
Wang, Z.; Yang, Y.; Gao, F.; Wang, Z.; Luo, Q.; Fang, L. Synthesis of 5-(trifluoromethyl) pyrazolines by formal [4+1] annulation of fluorinated sulfur ylides and azoalkenes. Org. Lett., 2018, 20, 934-937.
[33]
For selected examples with diazo compounds as one-carbon units in [4+1] annulations, see: (a) Zhou, J.-L.; Liang, Y.; Deng, C.; Zhou, H.; Wang, Z.; Sun, X.-L.; Zheng, J.-C.; Yu, Z.-X.; Tang, Y. Tunable carbonyl ylide reactions: selective synthesis of dihydrofurans and dihydrobenzoxepines. Angew. Chem. Int. Ed., 2011, 50, 7874-7878.
(b) Liu, C-R.; Zhu, B-H.; Zheng, J-C.; Sun, X-L.; Xieb, Z.; Tang, Y. Highly diastereroselective synthesis of dihydrofurans and dihydropyrroles viapyridine catalyzed formal [4+1] annulation. Chem. Commun., 2011, 47, 1342-1344.
[34]
Attanasi, O.A.; Crescentini, L.D.; Favi, G.; Mantellini, F.; Mantenuto, S.; Nicolini, S. Interceptive [4 + 1] annulation of in situ generated 1,2-diaza-1,3-dienes with diazo esters: direct access to substituted mono-, bi-, and tricyclic 4,5-dihydropyrazoles. J. Org. Chem., 2014, 79, 8331-8338.
[35]
Chen, D-Z.; Xiao, W-J.; Chen, J-R. Synthesis of piropyrazoline oxindoles by a formal [4 + 1] annulation reaction between 3-bromooxindoles and in situ-derived 1,2-diaza-1,3-dienes. Org. Chem. Front., 2017, 4, 1289-1293.
[36]
Bai, H-W.; Cai, Z-J.; Wang, S-Y.; Ji, S-J. Aerobic oxidative cycloaddition of α-chlorotosylhydrazones with arylamines: general chemoselective construction of 1,4-disubstituted and 1,5-disubstituted 1,2,3-triazoles under metal-free and azide-free conditions. Org. Lett., 2015, 17, 2898-2901.
[37]
Cai, Z-J.; Lu, X-M.; Zi, Y.; Yang, C.; Shen, L-J.; Li, J.; Wang, S-Y.; Ji, S-J.I. 2/TBPB mediated oxidative reaction of N-tosylhydrazones with anilines: practical construction of 1,4-disubstituted 1,2,3-triazoles under metal-free and azide-free conditions. Org. Lett., 2014, 16, 5108-5111.
[38]
Zhu, T-H.; Wei, T-Q.; Wang, S-Y.; Ji, S-J. NIS/CHP-mediated reaction of isocyanides with hydrazones: access to aminopyrazoles. Org. Chem. Front., 2015, 2, 259-264.
[39]
Wang, L.; Li, S.; Blîmel, M.; Philipps, A.R.; Wang, A.; Puttreddy, R.; Rissanen, K.; Enders, D. Asymmetric synthesis of spirobenzazepinones with atroposelectivity and spiro-1,2-diazepinones by NHC-catalyzed [3+4] annulation reactions. Angew. Chem. Int. Ed., 2016, 55, 11110-11114.
[40]
Hu, X-Q.; Chen, J-R.; Gao, S.; Feng, B.; Lu, L-Q.; Xiao, W-J. [4+3] Cycloaddition of in situ generated azoalkenes with C, N-cyclic azomethine imines: efficient synthesis of tetrazepine derivatives. Chem. Commun., 2013, 49, 7905-7907.
[41]
Yang, W.; Yuan, C.; Liu, Y.; Mao, B.; Sun, Z.; Guo, H. [4 + 3] Cycloaddition of phthalazinium dicyanomethanides with azoalkenes formed in situ: synthesis of triazepine derivatives. J. Org. Chem., 2016, 81, 7597-7603.
[42]
Gothelf, K.V.; Jørgensen, K.A. Catalytic enantioselective 1,3-dipolar cycloaddition reactions of nitrones. Chem. Commun., 2000, 0, 1449-1458.
[43]
Zhao, H-W.; Pang, H-L.; Tian, T.; Li, B.; Chen, X-Q.; Song, X-Q.; Meng, W.; Yang, Z.; Liu, Y-Y.; Zhao, Y-D. Construction of 2,3,4,7-tetrahydro-1,2,4,5-oxatriazepines via [4+3] cycloadditions of α-halogeno hydrazones with nitrones. Adv. Synth. Catal., 2016, 358, 1826-1832.
[44]
Wei, L.; Yao, L.; Wang, Z-F.; Li, H.; Tao, H-Y.; Wang, C-J. Copper(I)-catalyzed asymmetric 1,3-dipolar [3+4] cycloaddition of nitrones with azoalkenes. Adv. Synth. Catal., 2016, 358, 3748-3752.

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