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Supramolecular anion recognition mediates one-pot synthesis of 3-amino-[1,2,4]-triazolo pyridines from thiosemicarbazides

Supramolecular anion recognition mediates one-pot synthesis of 3-amino-[1,2,4]-triazolo pyridines from thiosemicarbazides
Supramolecular anion recognition mediates one-pot synthesis of 3-amino-[1,2,4]-triazolo pyridines from thiosemicarbazides
A facile one-pot synthesis of 3-amino-[1,2,4]-triazolo[4,3-a]pyridines from thiosemicarbazides through anion mediated synthesis is reported. Thiosemicarbazides derived from 2-hydrazino pyridine, 5-chloro 2-hydrazino pyridine, and 2-hydrazine quinoline were formed in situ as anion receptors in the presence of TBAF. Under microwave heating, thiosemicarbazides furnished the triazolo pyridines in good to moderate yields. The formation of the thiosemicarbazides hydrogen bonding anion receptors was critical in cascading the reaction toward the formation of the triazolo pyridines.
1523-7060
1068-1071
Pandurangan, Komala
c4eb9960-26ee-4ddf-886f-e4b193a18e4f
Aletti, Anna B.
f6de9dc9-b92b-4851-9e01-712a23f2a392
Devis, montroni
81533a52-5578-43a8-9470-9993d0b4740e
Kitchen, Jonathan
3999f5cb-d53e-4c51-b750-627bd2a1b9b6
Martínez-Calvo, Miguel
30469ce8-2b95-4bb4-9c48-d39c1038c411
Blasco, Salvador
2124f7c5-3285-4f6d-934a-ced2c607426b
Gunnlaugsson, Thorfinnur
bbfcaaa6-2aca-47c9-9b7b-954442218f50
Scanlan, Eoin M.
b2c6c33c-67e0-4290-ac88-46cf9ed00e17
Pandurangan, Komala
c4eb9960-26ee-4ddf-886f-e4b193a18e4f
Aletti, Anna B.
f6de9dc9-b92b-4851-9e01-712a23f2a392
Devis, montroni
81533a52-5578-43a8-9470-9993d0b4740e
Kitchen, Jonathan
3999f5cb-d53e-4c51-b750-627bd2a1b9b6
Martínez-Calvo, Miguel
30469ce8-2b95-4bb4-9c48-d39c1038c411
Blasco, Salvador
2124f7c5-3285-4f6d-934a-ced2c607426b
Gunnlaugsson, Thorfinnur
bbfcaaa6-2aca-47c9-9b7b-954442218f50
Scanlan, Eoin M.
b2c6c33c-67e0-4290-ac88-46cf9ed00e17

Pandurangan, Komala, Aletti, Anna B., Devis, montroni, Kitchen, Jonathan, Martínez-Calvo, Miguel, Blasco, Salvador, Gunnlaugsson, Thorfinnur and Scanlan, Eoin M. (2017) Supramolecular anion recognition mediates one-pot synthesis of 3-amino-[1,2,4]-triazolo pyridines from thiosemicarbazides. Organic Letters, 19 (5), 1068-1071. (doi:10.1021/acs.orglett.6b03645).

Record type: Article

Abstract

A facile one-pot synthesis of 3-amino-[1,2,4]-triazolo[4,3-a]pyridines from thiosemicarbazides through anion mediated synthesis is reported. Thiosemicarbazides derived from 2-hydrazino pyridine, 5-chloro 2-hydrazino pyridine, and 2-hydrazine quinoline were formed in situ as anion receptors in the presence of TBAF. Under microwave heating, thiosemicarbazides furnished the triazolo pyridines in good to moderate yields. The formation of the thiosemicarbazides hydrogen bonding anion receptors was critical in cascading the reaction toward the formation of the triazolo pyridines.

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Org Lett 2017 Final_revised2 - Accepted Manuscript
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Accepted/In Press date: 17 February 2017
e-pub ahead of print date: 21 February 2017
Organisations: FIMS

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Local EPrints ID: 407949
URI: https://eprints.soton.ac.uk/id/eprint/407949
ISSN: 1523-7060
PURE UUID: de83e75f-5e8c-44be-9343-564015c851c3
ORCID for Jonathan Kitchen: ORCID iD orcid.org/0000-0002-7139-5666

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Date deposited: 05 May 2017 01:03
Last modified: 10 Sep 2019 04:55

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Contributors

Author: Komala Pandurangan
Author: Anna B. Aletti
Author: montroni Devis
Author: Jonathan Kitchen ORCID iD
Author: Miguel Martínez-Calvo
Author: Salvador Blasco
Author: Thorfinnur Gunnlaugsson
Author: Eoin M. Scanlan

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