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CDC reactions of N-aryl tetrahydroisoquinolines using catalytic amounts of DDQ: C-H activation under aerobic conditions.

Chemistry (Weinheim an der Bergstrasse, Germany)

Alagiri K, Devadig P, Prabhu KR.
PMID: 22431410
Chemistry. 2012 Apr 23;18(17):5160-4. doi: 10.1002/chem.201200100. Epub 2012 Mar 19.

No abstract available.

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Alagiri K, Devadig P, Prabhu KR. CDC reactions of N-aryl tetrahydroisoquinolines using catalytic amounts of DDQ: C-H activation under aerobic conditions. Chemistry. 2012;18(17):5160-4doi: 10.1002/chem.201200100.
Alagiri, K., Devadig, P., & Prabhu, K. R. (2012). CDC reactions of N-aryl tetrahydroisoquinolines using catalytic amounts of DDQ: C-H activation under aerobic conditions. Chemistry (Weinheim an der Bergstrasse, Germany), 18(17), 5160-4. https://doi.org/10.1002/chem.201200100
Alagiri, Kaliyamoorthy, et al. "CDC reactions of N-aryl tetrahydroisoquinolines using catalytic amounts of DDQ: C-H activation under aerobic conditions." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 18,17 (2012): 5160-4. doi: https://doi.org/10.1002/chem.201200100
Alagiri K, Devadig P, Prabhu KR. CDC reactions of N-aryl tetrahydroisoquinolines using catalytic amounts of DDQ: C-H activation under aerobic conditions. Chemistry. 2012 Apr 23;18(17):5160-4. doi: 10.1002/chem.201200100. Epub 2012 Mar 19. PMID: 22431410.
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Catalytic Asymmetric Electrochemical Oxidative Coupling of Tertiary Amines with Simple Ketones.

Organic letters

Fu N, Li L, Yang Q, Luo S.
PMID: 28394132
Org Lett. 2017 Apr 21;19(8):2122-2125. doi: 10.1021/acs.orglett.7b00746. Epub 2017 Apr 10.

Catalytic asymmetric electrochemical C-H functionalization of simple ketones has been developed. The transformation is realized by the combination of electrochemical oxidation and chiral primary amine catalysis. This metal- and oxidant-free method furnishes diverse C1-alkylated tetrahydroisoquinolines in high yields and...

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Fu N, Li L, Yang Q, et al. Catalytic Asymmetric Electrochemical Oxidative Coupling of Tertiary Amines with Simple Ketones. Org Lett. 2017;19(8):2122-2125doi: 10.1021/acs.orglett.7b00746.
Fu, N., Li, L., Yang, Q., & Luo, S. (2017). Catalytic Asymmetric Electrochemical Oxidative Coupling of Tertiary Amines with Simple Ketones. Organic letters, 19(8), 2122-2125. https://doi.org/10.1021/acs.orglett.7b00746
Fu, Niankai, et al. "Catalytic Asymmetric Electrochemical Oxidative Coupling of Tertiary Amines with Simple Ketones." Organic letters vol. 19,8 (2017): 2122-2125. doi: https://doi.org/10.1021/acs.orglett.7b00746
Fu N, Li L, Yang Q, Luo S. Catalytic Asymmetric Electrochemical Oxidative Coupling of Tertiary Amines with Simple Ketones. Org Lett. 2017 Apr 21;19(8):2122-2125. doi: 10.1021/acs.orglett.7b00746. Epub 2017 Apr 10. PMID: 28394132.
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Redox condensation of o-halonitrobenzene with 1,2,3,4-tetrahydroisoquinoline: involvement of an unexpected auto-catalyzed redox cascade.

Chemical communications (Cambridge, England)

Nguyen TB, Ermolenko L, Al-Mourabit A.
PMID: 26975797
Chem Commun (Camb). 2016 Apr 07;52(27):4914-7. doi: 10.1039/c6cc01436d. Epub 2016 Mar 15.

A practical synthesis of fused benzimidazoles 5 has been developed by simply heating o-halonitrobenzenes 1 with tetrahydroisoquinolines 2. In this transformation, 2 played multiple roles as a building block, base and a double hydride donor in a cascade of...

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Nguyen TB, Ermolenko L, Al-Mourabit A. Redox condensation of o-halonitrobenzene with 1,2,3,4-tetrahydroisoquinoline: involvement of an unexpected auto-catalyzed redox cascade. Chem Commun (Camb). 2016;52(27):4914-7doi: 10.1039/c6cc01436d.
Nguyen, T. B., Ermolenko, L., & Al-Mourabit, A. (2016). Redox condensation of o-halonitrobenzene with 1,2,3,4-tetrahydroisoquinoline: involvement of an unexpected auto-catalyzed redox cascade. Chemical communications (Cambridge, England), 52(27), 4914-7. https://doi.org/10.1039/c6cc01436d
Nguyen, T B, et al. "Redox condensation of o-halonitrobenzene with 1,2,3,4-tetrahydroisoquinoline: involvement of an unexpected auto-catalyzed redox cascade." Chemical communications (Cambridge, England) vol. 52,27 (2016): 4914-7. doi: https://doi.org/10.1039/c6cc01436d
Nguyen TB, Ermolenko L, Al-Mourabit A. Redox condensation of o-halonitrobenzene with 1,2,3,4-tetrahydroisoquinoline: involvement of an unexpected auto-catalyzed redox cascade. Chem Commun (Camb). 2016 Apr 07;52(27):4914-7. doi: 10.1039/c6cc01436d. Epub 2016 Mar 15. PMID: 26975797.
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Metal-Free Activation of a C(sp)-H Bond of Aryl Acetylenes.

Chemistry (Weinheim an der Bergstrasse, Germany)

Rout L, Parida BB, Florent JC, Johannes L, Choudhury SK, Phaomei G, Scanlon J, Bertounesque E.
PMID: 27504988
Chemistry. 2016 Oct 10;22(42):14812-14815. doi: 10.1002/chem.201603003. Epub 2016 Aug 30.

C(sp)-H Bond activation of acetylene molecule still remains a challenge for synthetic organic chemists. In practice, acetylenes are activated by strong bases and metals. The first example for activating acetylenic protons under base and metal-free conditions is reported here....

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Rout L, Parida BB, Florent JC, et al. Metal-Free Activation of a C(sp)-H Bond of Aryl Acetylenes. Chemistry. 2016;22(42):14812-14815doi: 10.1002/chem.201603003.
Rout, L., Parida, B. B., Florent, J. C., Johannes, L., Choudhury, S. K., Phaomei, G., Scanlon, J., & Bertounesque, E. (2016). Metal-Free Activation of a C(sp)-H Bond of Aryl Acetylenes. Chemistry (Weinheim an der Bergstrasse, Germany), 22(42), 14812-14815. https://doi.org/10.1002/chem.201603003
Rout, Laxmidhar, et al. "Metal-Free Activation of a C(sp)-H Bond of Aryl Acetylenes." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,42 (2016): 14812-14815. doi: https://doi.org/10.1002/chem.201603003
Rout L, Parida BB, Florent JC, Johannes L, Choudhury SK, Phaomei G, Scanlon J, Bertounesque E. Metal-Free Activation of a C(sp)-H Bond of Aryl Acetylenes. Chemistry. 2016 Oct 10;22(42):14812-14815. doi: 10.1002/chem.201603003. Epub 2016 Aug 30. PMID: 27504988.
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Oxazolidines as Intermediates in the Asymmetric Synthesis of 3-Substituted and 1,3-Disubstituted Tetrahydroisoquinolines.

The Journal of organic chemistry

Raghavan S, Senapati P.
PMID: 27404666
J Org Chem. 2016 Aug 05;81(15):6201-10. doi: 10.1021/acs.joc.6b00525. Epub 2016 Jul 26.

A diastereoselective mercury(II)-promoted intramolecular cyclization of unsaturated aldehyde via an oxazolidine to prepare C-3-substituted tetrahydroisoquinoline is disclosed. The C-3 stereogenic center is subsequently exploited to create the C-1 stereocenter by coordination of the nucleophilic reagent to the oxygen atom...

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Raghavan S, Senapati P. Oxazolidines as Intermediates in the Asymmetric Synthesis of 3-Substituted and 1,3-Disubstituted Tetrahydroisoquinolines. J Org Chem. 2016;81(15):6201-10doi: 10.1021/acs.joc.6b00525.
Raghavan, S., & Senapati, P. (2016). Oxazolidines as Intermediates in the Asymmetric Synthesis of 3-Substituted and 1,3-Disubstituted Tetrahydroisoquinolines. The Journal of organic chemistry, 81(15), 6201-10. https://doi.org/10.1021/acs.joc.6b00525
Raghavan, Sadagopan, and Senapati, Puspamitra. "Oxazolidines as Intermediates in the Asymmetric Synthesis of 3-Substituted and 1,3-Disubstituted Tetrahydroisoquinolines." The Journal of organic chemistry vol. 81,15 (2016): 6201-10. doi: https://doi.org/10.1021/acs.joc.6b00525
Raghavan S, Senapati P. Oxazolidines as Intermediates in the Asymmetric Synthesis of 3-Substituted and 1,3-Disubstituted Tetrahydroisoquinolines. J Org Chem. 2016 Aug 05;81(15):6201-10. doi: 10.1021/acs.joc.6b00525. Epub 2016 Jul 26. PMID: 27404666.
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Approach to Isoindolinones, Isoquinolinones, and THIQs via Lewis Acid-Catalyzed Domino Strecker-Lactamization/Alkylations.

Organic letters

Dhanasekaran S, Suneja A, Bisai V, Singh VK.
PMID: 26843100
Org Lett. 2016 Feb 19;18(4):634-7. doi: 10.1021/acs.orglett.5b03331. Epub 2016 Feb 04.

A one-pot, three-component synthesis of widely substituted isoindolinones and isoquinolinones, featuring a Lewis acid-catalyzed efficient Strecker reaction and lactamization sequence, affording products in good to high yields is reported. The method has also been extended to the synthesis of...

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Dhanasekaran S, Suneja A, Bisai V, et al. Approach to Isoindolinones, Isoquinolinones, and THIQs via Lewis Acid-Catalyzed Domino Strecker-Lactamization/Alkylations. Org Lett. 2016;18(4):634-7doi: 10.1021/acs.orglett.5b03331.
Dhanasekaran, S., Suneja, A., Bisai, V., & Singh, V. K. (2016). Approach to Isoindolinones, Isoquinolinones, and THIQs via Lewis Acid-Catalyzed Domino Strecker-Lactamization/Alkylations. Organic letters, 18(4), 634-7. https://doi.org/10.1021/acs.orglett.5b03331
Dhanasekaran, Sivasankaran, et al. "Approach to Isoindolinones, Isoquinolinones, and THIQs via Lewis Acid-Catalyzed Domino Strecker-Lactamization/Alkylations." Organic letters vol. 18,4 (2016): 634-7. doi: https://doi.org/10.1021/acs.orglett.5b03331
Dhanasekaran S, Suneja A, Bisai V, Singh VK. Approach to Isoindolinones, Isoquinolinones, and THIQs via Lewis Acid-Catalyzed Domino Strecker-Lactamization/Alkylations. Org Lett. 2016 Feb 19;18(4):634-7. doi: 10.1021/acs.orglett.5b03331. Epub 2016 Feb 04. PMID: 26843100.
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Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates.

Chemistry (Weinheim an der Bergstrasse, Germany)

Wang Y, Wang Q, Zhu J.
PMID: 27135440
Chemistry. 2016 Jun 06;22(24):8084-8. doi: 10.1002/chem.201601548. Epub 2016 May 02.

The first catalytic asymmetric inverse electron demand 1,3-dipolar cycloaddition of azomethine imines with enecarbamates has been developed. Isoquinoline-fused pyrazolidines containing two or three contiguous stereogenic centers were obtained in high yields with excellent regio-, diastereo-, and enantioselectivities. The pyrazolidine...

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Wang Y, Wang Q, Zhu J. Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates. Chemistry. 2016;22(24):8084-8doi: 10.1002/chem.201601548.
Wang, Y., Wang, Q., & Zhu, J. (2016). Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates. Chemistry (Weinheim an der Bergstrasse, Germany), 22(24), 8084-8. https://doi.org/10.1002/chem.201601548
Wang, Yang, et al. "Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 22,24 (2016): 8084-8. doi: https://doi.org/10.1002/chem.201601548
Wang Y, Wang Q, Zhu J. Chiral Phosphoric Acid-Catalyzed Enantioselective Formal [3+2] Cycloaddition of Azomethine Imines with Enecarbamates. Chemistry. 2016 Jun 06;22(24):8084-8. doi: 10.1002/chem.201601548. Epub 2016 May 02. PMID: 27135440.
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Design and synthesis of 4-heteroaryl 1,2,3,4-tetrahydroisoquinolines as triple reuptake inhibitors.

ACS medicinal chemistry letters

Liu S, Zha C, Nacro K, Hu M, Cui W, Yang YL, Bhatt U, Sambandam A, Isherwood M, Yet L, Herr MT, Ebeltoft S, Hassler C, Fleming L, Pechulis AD, Payen-Fornicola A, Holman N, Milanowski D, Cotterill I, Mozhaev V, Khmelnitsky Y, Guzzo PR, Sargent BJ, Molino BF, Olson R, King D, Lelas S, Li YW, Johnson K, Molski T, Orie A, Ng A, Haskell R, Clarke W, Bertekap R, O'Connell J, Lodge N, Sinz M, Adams S, Zaczek R, Macor JE.
PMID: 25050161
ACS Med Chem Lett. 2014 May 13;5(7):760-5. doi: 10.1021/ml500053b. eCollection 2014 Jul 10.

A series of 4-bicyclic heteroaryl 1,2,3,4-tetrahydroisoquinoline inhibitors of the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT) was discovered. The synthesis and structure-activity relationship (SAR) of these triple reuptake inhibitors (TRIs) will be discussed. Compound 10i (AMR-2),...

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Liu S, Zha C, Nacro K, et al. Design and synthesis of 4-heteroaryl 1,2,3,4-tetrahydroisoquinolines as triple reuptake inhibitors. ACS Med Chem Lett. 2014;5(7):760-5doi: 10.1021/ml500053b.
Liu, S., Zha, C., Nacro, K., Hu, M., Cui, W., Yang, Y. L., Bhatt, U., Sambandam, A., Isherwood, M., Yet, L., Herr, M. T., Ebeltoft, S., Hassler, C., Fleming, L., Pechulis, A. D., Payen-Fornicola, A., Holman, N., Milanowski, D., Cotterill, I., Mozhaev, V., Khmelnitsky, Y., Guzzo, P. R., Sargent, B. J., Molino, B. F., Olson, R., King, D., Lelas, S., Li, Y. W., Johnson, K., Molski, T., Orie, A., Ng, A., Haskell, R., Clarke, W., Bertekap, R., O'Connell, J., Lodge, N., Sinz, M., Adams, S., Zaczek, R., & Macor, J. E. (2014). Design and synthesis of 4-heteroaryl 1,2,3,4-tetrahydroisoquinolines as triple reuptake inhibitors. ACS medicinal chemistry letters, 5(7), 760-5. https://doi.org/10.1021/ml500053b
Liu, Shuang, et al. "Design and synthesis of 4-heteroaryl 1,2,3,4-tetrahydroisoquinolines as triple reuptake inhibitors." ACS medicinal chemistry letters vol. 5,7 (2014): 760-5. doi: https://doi.org/10.1021/ml500053b
Liu S, Zha C, Nacro K, Hu M, Cui W, Yang YL, Bhatt U, Sambandam A, Isherwood M, Yet L, Herr MT, Ebeltoft S, Hassler C, Fleming L, Pechulis AD, Payen-Fornicola A, Holman N, Milanowski D, Cotterill I, Mozhaev V, Khmelnitsky Y, Guzzo PR, Sargent BJ, Molino BF, Olson R, King D, Lelas S, Li YW, Johnson K, Molski T, Orie A, Ng A, Haskell R, Clarke W, Bertekap R, O'Connell J, Lodge N, Sinz M, Adams S, Zaczek R, Macor JE. Design and synthesis of 4-heteroaryl 1,2,3,4-tetrahydroisoquinolines as triple reuptake inhibitors. ACS Med Chem Lett. 2014 May 13;5(7):760-5. doi: 10.1021/ml500053b. eCollection 2014 Jul 10. PMID: 25050161; PMCID: PMC4094255.
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Pd(0)-catalyzed regio- and stereoselective cyclization of alkynes: selective synthesis of (E)-4-(isobenzofuran-1(3H)-ylidene)-1,2,3,4-tetrahydroisoquinolines and aze/oxepinoindoles.

Organic & biomolecular chemistry

Nandakumar A, Kiruthika SE, Naveen K, Perumal PT.
PMID: 24357272
Org Biomol Chem. 2014 Feb 14;12(6):876-80. doi: 10.1039/c3ob42314j.

Palladium-catalyzed highly regio- and stereoselective 6-exo-dig and 7-endo-dig cyclization of functionalized propargylic compounds has been developed for the synthesis of (E)-4-(isobenzofuran-1(3H)-ylidene)-1,2,3,4-tetrahydroisoquinolines and aze/oxepinoindoles.

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Nandakumar A, Kiruthika SE, Naveen K, et al. Pd(0)-catalyzed regio- and stereoselective cyclization of alkynes: selective synthesis of (E)-4-(isobenzofuran-1(3H)-ylidene)-1,2,3,4-tetrahydroisoquinolines and aze/oxepinoindoles. Org Biomol Chem. 2014;12(6):876-80doi: 10.1039/c3ob42314j.
Nandakumar, A., Kiruthika, S. E., Naveen, K., & Perumal, P. T. (2014). Pd(0)-catalyzed regio- and stereoselective cyclization of alkynes: selective synthesis of (E)-4-(isobenzofuran-1(3H)-ylidene)-1,2,3,4-tetrahydroisoquinolines and aze/oxepinoindoles. Organic & biomolecular chemistry, 12(6), 876-80. https://doi.org/10.1039/c3ob42314j
Nandakumar, Avanashiappan, et al. "Pd(0)-catalyzed regio- and stereoselective cyclization of alkynes: selective synthesis of (E)-4-(isobenzofuran-1(3H)-ylidene)-1,2,3,4-tetrahydroisoquinolines and aze/oxepinoindoles." Organic & biomolecular chemistry vol. 12,6 (2014): 876-80. doi: https://doi.org/10.1039/c3ob42314j
Nandakumar A, Kiruthika SE, Naveen K, Perumal PT. Pd(0)-catalyzed regio- and stereoselective cyclization of alkynes: selective synthesis of (E)-4-(isobenzofuran-1(3H)-ylidene)-1,2,3,4-tetrahydroisoquinolines and aze/oxepinoindoles. Org Biomol Chem. 2014 Feb 14;12(6):876-80. doi: 10.1039/c3ob42314j. PMID: 24357272.
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One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates.

Beilstein journal of organic chemistry

Barham JP, John MP, Murphy JA.
PMID: 25550765
Beilstein J Org Chem. 2014 Dec 12;10:2981-8. doi: 10.3762/bjoc.10.316. eCollection 2014.

Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology...

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Barham JP, John MP, Murphy JA. One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates. Beilstein J Org Chem. 2014;10:2981-8doi: 10.3762/bjoc.10.316.
Barham, J. P., John, M. P., & Murphy, J. A. (2014). One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates. Beilstein journal of organic chemistry, 102981-8. https://doi.org/10.3762/bjoc.10.316
Barham, Joshua P, et al. "One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates." Beilstein journal of organic chemistry vol. 10 (2014): 2981-8. doi: https://doi.org/10.3762/bjoc.10.316
Barham JP, John MP, Murphy JA. One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates. Beilstein J Org Chem. 2014 Dec 12;10:2981-8. doi: 10.3762/bjoc.10.316. eCollection 2014. PMID: 25550765; PMCID: PMC4273301.
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Collision-induced dissociation of phenethylamides: role of ion-neutral complexes.

Rapid communications in mass spectrometry : RCM

Nikolić D, Macias C, Lankin DC, van Breemen RB.
PMID: 28558170
Rapid Commun Mass Spectrom. 2017 Sep 15;31(17):1385-1395. doi: 10.1002/rcm.7915.

RATIONALE: Phenethylamides are a large group of naturally occurring molecules found both in the plant and animal kingdoms. In addition, they are used as intermediates for the synthesis of pharmaceutically important dihydro- and tetrahydroisoquinolines. To enable efficient characterization of...

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Nikolić D, Macias C, Lankin DC, et al. Collision-induced dissociation of phenethylamides: role of ion-neutral complexes. Rapid Commun Mass Spectrom. 2017;31(17):1385-1395doi: 10.1002/rcm.7915.
Nikolić, D., Macias, C., Lankin, D. C., & van Breemen, R. B. (2017). Collision-induced dissociation of phenethylamides: role of ion-neutral complexes. Rapid communications in mass spectrometry : RCM, 31(17), 1385-1395. https://doi.org/10.1002/rcm.7915
Nikolić, Dejan, et al. "Collision-induced dissociation of phenethylamides: role of ion-neutral complexes." Rapid communications in mass spectrometry : RCM vol. 31,17 (2017): 1385-1395. doi: https://doi.org/10.1002/rcm.7915
Nikolić D, Macias C, Lankin DC, van Breemen RB. Collision-induced dissociation of phenethylamides: role of ion-neutral complexes. Rapid Commun Mass Spectrom. 2017 Sep 15;31(17):1385-1395. doi: 10.1002/rcm.7915. PMID: 28558170; PMCID: PMC5555735.
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Enzyme catalysed Pictet-Spengler formation of chiral 1,1'-disubstituted- and spiro-tetrahydroisoquinolines.

Nature communications

Lichman BR, Zhao J, Hailes HC, Ward JM.
PMID: 28368003
Nat Commun. 2017 Apr 03;8:14883. doi: 10.1038/ncomms14883.

The Pictet-Spengler reaction (PSR) involves the condensation and ring closure between a β-arylethylamine and a carbonyl compound. The combination of dopamine and ketones in a PSR leads to the formation of 1,1'-disubstituted tetrahydroisoquinolines (THIQs), structures that are challenging to...

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Lichman BR, Zhao J, Hailes HC, et al. Enzyme catalysed Pictet-Spengler formation of chiral 1,1'-disubstituted- and spiro-tetrahydroisoquinolines. Nat Commun. 2017;8:14883doi: 10.1038/ncomms14883.
Lichman, B. R., Zhao, J., Hailes, H. C., & Ward, J. M. (2017). Enzyme catalysed Pictet-Spengler formation of chiral 1,1'-disubstituted- and spiro-tetrahydroisoquinolines. Nature communications, 814883. https://doi.org/10.1038/ncomms14883
Lichman, Benjamin R, et al. "Enzyme catalysed Pictet-Spengler formation of chiral 1,1'-disubstituted- and spiro-tetrahydroisoquinolines." Nature communications vol. 8 (2017): 14883. doi: https://doi.org/10.1038/ncomms14883
Lichman BR, Zhao J, Hailes HC, Ward JM. Enzyme catalysed Pictet-Spengler formation of chiral 1,1'-disubstituted- and spiro-tetrahydroisoquinolines. Nat Commun. 2017 Apr 03;8:14883. doi: 10.1038/ncomms14883. PMID: 28368003; PMCID: PMC5382262.
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