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Synthesis of Spiro[chromene-imidazo[1,2-a]pyridin]-3′-imines via 6-exo-dig Cyclization Reaction. / Nayebzadeh, Behrouz; Amiri, Kamran; Khosravi, Hormoz; Mirzaei, Saber; Rominger, Frank; Dar'in, Dmitry; Krasavin, Mikhail; Bijanzadeh, Hamid Reza; Balalaie, Saeed.

In: Journal of Organic Chemistry, Vol. 86, No. 19, 01.10.2021, p. 13693–13701.

Research output: Contribution to journal › Article › peer-review

Harvard

Nayebzadeh, B, Amiri, K, Khosravi, H, Mirzaei, S, Rominger, F, Dar'in, D, Krasavin, M, Bijanzadeh, HR & Balalaie, S 2021, 'Synthesis of Spiro[chromene-imidazo[1,2-a]pyridin]-3′-imines via 6-exo-dig Cyclization Reaction', Journal of Organic Chemistry, vol. 86, no. 19, pp. 13693–13701. https://doi.org/10.1021/acs.joc.1c01789

APA

Nayebzadeh, B., Amiri, K., Khosravi, H., Mirzaei, S., Rominger, F., Dar'in, D., Krasavin, M., Bijanzadeh, H. R., & Balalaie, S. (2021). Synthesis of Spiro[chromene-imidazo[1,2-a]pyridin]-3′-imines via 6-exo-dig Cyclization Reaction. Journal of Organic Chemistry, 86(19), 13693–13701. https://doi.org/10.1021/acs.joc.1c01789

Vancouver

Nayebzadeh B, Amiri K, Khosravi H, Mirzaei S, Rominger F, Dar'in D et al. Synthesis of Spiro[chromene-imidazo[1,2-a]pyridin]-3′-imines via 6-exo-dig Cyclization Reaction. Journal of Organic Chemistry. 2021 Oct 1;86(19):13693–13701. https://doi.org/10.1021/acs.joc.1c01789

Author

Nayebzadeh, Behrouz ; Amiri, Kamran ; Khosravi, Hormoz ; Mirzaei, Saber ; Rominger, Frank ; Dar'in, Dmitry ; Krasavin, Mikhail ; Bijanzadeh, Hamid Reza ; Balalaie, Saeed. / Synthesis of Spiro[chromene-imidazo[1,2-a]pyridin]-3′-imines via 6-exo-dig Cyclization Reaction. In: Journal of Organic Chemistry. 2021 ; Vol. 86, No. 19. pp. 13693–13701.

BibTeX

@article{695fad3f9dfd4bc785e50596641ac5c5,
title = "Synthesis of Spiro[chromene-imidazo[1,2-a]pyridin]-3′-imines via 6-exo-dig Cyclization Reaction",
abstract = "A transition-metal-free postmodification of the Groebke-Blackburn-Bienaym{\'e} (GBB) reaction for the synthesis of spiro[chromene-imidazo[1,2-A]pyridin]-3′-imine was discovered. The unusual transformation represents the first example of activation and the reaction of the imidazole carbon atom. In this postcondensational modification, KOt-Bu acts as a base, which, after the isomerization of an alkyne moiety to allene, causes the next unique nucleophilic reaction of the imidazole carbon atom that results in spirocyclic structures. The proposed reaction mechanism was confirmed based on the DFT calculations. ",
keywords = "DIELS-ALDER REACTION, MULTICOMPONENT REACTIONS, DIASTEREOSELECTIVE SYNTHESIS, 3-COMPONENT, DERIVATIVES, CHEMISTRY, PYRAZINES, ALKYNES",
author = "Behrouz Nayebzadeh and Kamran Amiri and Hormoz Khosravi and Saber Mirzaei and Frank Rominger and Dmitry Dar'in and Mikhail Krasavin and Bijanzadeh, {Hamid Reza} and Saeed Balalaie",
note = "Publisher Copyright: {\textcopyright} ",
year = "2021",
month = oct,
day = "1",
doi = "10.1021/acs.joc.1c01789",
language = "English",
volume = "86",
pages = "13693–13701",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "19",

}

RIS

TY - JOUR

T1 - Synthesis of Spiro[chromene-imidazo[1,2-a]pyridin]-3′-imines via 6-exo-dig Cyclization Reaction

AU - Nayebzadeh, Behrouz

AU - Amiri, Kamran

AU - Khosravi, Hormoz

AU - Mirzaei, Saber

AU - Rominger, Frank

AU - Dar'in, Dmitry

AU - Krasavin, Mikhail

AU - Bijanzadeh, Hamid Reza

AU - Balalaie, Saeed

N1 - Publisher Copyright: ©

PY - 2021/10/1

Y1 - 2021/10/1

N2 - A transition-metal-free postmodification of the Groebke-Blackburn-Bienaymé (GBB) reaction for the synthesis of spiro[chromene-imidazo[1,2-A]pyridin]-3′-imine was discovered. The unusual transformation represents the first example of activation and the reaction of the imidazole carbon atom. In this postcondensational modification, KOt-Bu acts as a base, which, after the isomerization of an alkyne moiety to allene, causes the next unique nucleophilic reaction of the imidazole carbon atom that results in spirocyclic structures. The proposed reaction mechanism was confirmed based on the DFT calculations.

AB - A transition-metal-free postmodification of the Groebke-Blackburn-Bienaymé (GBB) reaction for the synthesis of spiro[chromene-imidazo[1,2-A]pyridin]-3′-imine was discovered. The unusual transformation represents the first example of activation and the reaction of the imidazole carbon atom. In this postcondensational modification, KOt-Bu acts as a base, which, after the isomerization of an alkyne moiety to allene, causes the next unique nucleophilic reaction of the imidazole carbon atom that results in spirocyclic structures. The proposed reaction mechanism was confirmed based on the DFT calculations.

KW - DIELS-ALDER REACTION

KW - MULTICOMPONENT REACTIONS

KW - DIASTEREOSELECTIVE SYNTHESIS

KW - 3-COMPONENT

KW - DERIVATIVES

KW - CHEMISTRY

KW - PYRAZINES

KW - ALKYNES

UR - http://www.scopus.com/inward/record.url?scp=85115944420&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.1c01789

DO - 10.1021/acs.joc.1c01789

M3 - Article

AN - SCOPUS:85115944420

VL - 86

SP - 13693

EP - 13701

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 19

ER -

ID: 86412774