TfOH catalyzed One-Pot Schmidt–Ritter reaction for the synthesis of amides through N-acylimides

Garima Singh; Ravikrishna Dada; Srinivasarao Yaragorla

doi:10.1016/j.tetlet.2016.08.069

TfOH catalyzed One-Pot Schmidt–Ritter reaction for the synthesis of amides through N-acylimides

Garima Singh, Ravikrishna Dada, Srinivasarao Yaragorla

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

19 Scopus citations

Abstract

A One-Pot tandem Schmidt–Ritter process for the synthesis of amides has been developed using the super acid as catalyst. The in situ generated aryl/aliphatic nitriles from the reaction of aldehydes and sodium azide in the presence of TfOH and AcOH (Schmidt reaction) react with suitable alcohol (Ritter reaction) to give the amides. For the first time we observed that during the Schmidt process N-acylimides were generated along with nitriles, interestingly these N-acylimides also participated in the Ritter reaction.

Original language	English (US)
Pages (from-to)	4424-4427
Number of pages	4
Journal	Tetrahedron Letters
Volume	57
Issue number	39
DOIs	https://doi.org/10.1016/j.tetlet.2016.08.069
State	Published - 2016
Externally published	Yes

Bibliographical note

Funding Information:
GS and RD thank Central University of Rajasthan for the fellowship and SY thank Council of Scientific and Industrial Research (CSIR)-India for the financial support under Extramural Research Grant-No. 02(0200)/14/EMR-II .

Publisher Copyright:
© 2016 Elsevier Ltd

Keywords

Amides
Multicomponent reaction
N-Acylimides
Schmidt–Ritter reaction
TfOH

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10.1016/j.tetlet.2016.08.069

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title = "TfOH catalyzed One-Pot Schmidt–Ritter reaction for the synthesis of amides through N-acylimides",

abstract = "A One-Pot tandem Schmidt–Ritter process for the synthesis of amides has been developed using the super acid as catalyst. The in situ generated aryl/aliphatic nitriles from the reaction of aldehydes and sodium azide in the presence of TfOH and AcOH (Schmidt reaction) react with suitable alcohol (Ritter reaction) to give the amides. For the first time we observed that during the Schmidt process N-acylimides were generated along with nitriles, interestingly these N-acylimides also participated in the Ritter reaction.",

keywords = "Amides, Multicomponent reaction, N-Acylimides, Schmidt–Ritter reaction, TfOH",

author = "Garima Singh and Ravikrishna Dada and Srinivasarao Yaragorla",

note = "Funding Information: GS and RD thank Central University of Rajasthan for the fellowship and SY thank Council of Scientific and Industrial Research (CSIR)-India for the financial support under Extramural Research Grant-No. 02(0200)/14/EMR-II . Publisher Copyright: {\textcopyright} 2016 Elsevier Ltd",

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doi = "10.1016/j.tetlet.2016.08.069",

language = "English (US)",

volume = "57",

pages = "4424--4427",

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TY - JOUR

T1 - TfOH catalyzed One-Pot Schmidt–Ritter reaction for the synthesis of amides through N-acylimides

AU - Singh, Garima

AU - Dada, Ravikrishna

AU - Yaragorla, Srinivasarao

N1 - Funding Information: GS and RD thank Central University of Rajasthan for the fellowship and SY thank Council of Scientific and Industrial Research (CSIR)-India for the financial support under Extramural Research Grant-No. 02(0200)/14/EMR-II . Publisher Copyright: © 2016 Elsevier Ltd

PY - 2016

Y1 - 2016

N2 - A One-Pot tandem Schmidt–Ritter process for the synthesis of amides has been developed using the super acid as catalyst. The in situ generated aryl/aliphatic nitriles from the reaction of aldehydes and sodium azide in the presence of TfOH and AcOH (Schmidt reaction) react with suitable alcohol (Ritter reaction) to give the amides. For the first time we observed that during the Schmidt process N-acylimides were generated along with nitriles, interestingly these N-acylimides also participated in the Ritter reaction.

AB - A One-Pot tandem Schmidt–Ritter process for the synthesis of amides has been developed using the super acid as catalyst. The in situ generated aryl/aliphatic nitriles from the reaction of aldehydes and sodium azide in the presence of TfOH and AcOH (Schmidt reaction) react with suitable alcohol (Ritter reaction) to give the amides. For the first time we observed that during the Schmidt process N-acylimides were generated along with nitriles, interestingly these N-acylimides also participated in the Ritter reaction.

KW - Amides

KW - Multicomponent reaction

KW - N-Acylimides

KW - Schmidt–Ritter reaction

KW - TfOH

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U2 - 10.1016/j.tetlet.2016.08.069

DO - 10.1016/j.tetlet.2016.08.069

M3 - Article

AN - SCOPUS:84985918604

SN - 0040-4039

VL - 57

SP - 4424

EP - 4427

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 39

ER -

TfOH catalyzed One-Pot Schmidt–Ritter reaction for the synthesis of amides through N-acylimides

Abstract

Bibliographical note

Keywords

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