Facile synthesis of 1-substituted 2-amino-3-cyanopyrroles: New synthetic precursors for 5,6-unsubstituted pyrrolo[2,3-d]pyrimidines

Tun-Cheng Chien, Eric A. Meade, Jack M. Hinkley, Leroy B. Townsend

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

(Equation Presented) 1-Benzyl-3-cyanopyrrole-2-carbonyl azide (5) underwent a Curtius rearrangement followed by quenching with alcohols to form the corresponding carbamates (6a-c). The carbamates 6a,b were unblocked to give the desired 2-amino-1-benzyl-3-cyanopyrrole (1a). A more facile procedure was subsequently developed for the synthesis of 1-substituted 2-amino-3- cyanopyrroles. N-Substituted aminoacetaldehyde dimethyl acetals (7a-c) were condensed with malononitrile in the presence of p-toluenesulfonic acid monohydrate to afford the corresponding 1-substituted 2-amino-3-cyanopyrroles (1a-c).

Original languageEnglish
Pages (from-to)2857-2859
Number of pages3
JournalOrganic Letters
Volume6
Issue number17
DOIs
Publication statusPublished - 2004 Aug 19

Fingerprint

Carbamates
pyrimidines
malononitrile
acetals
Azides
synthesis
Quenching
alcohols
quenching
Alcohols
acids
Pyrrolo(2,3-d)pyrimidine
4-toluenesulfonic acid
dicyanmethane
1,1-dimethoxyethane

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Facile synthesis of 1-substituted 2-amino-3-cyanopyrroles : New synthetic precursors for 5,6-unsubstituted pyrrolo[2,3-d]pyrimidines. / Chien, Tun-Cheng; Meade, Eric A.; Hinkley, Jack M.; Townsend, Leroy B.

In: Organic Letters, Vol. 6, No. 17, 19.08.2004, p. 2857-2859.

Research output: Contribution to journalArticle

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abstract = "(Equation Presented) 1-Benzyl-3-cyanopyrrole-2-carbonyl azide (5) underwent a Curtius rearrangement followed by quenching with alcohols to form the corresponding carbamates (6a-c). The carbamates 6a,b were unblocked to give the desired 2-amino-1-benzyl-3-cyanopyrrole (1a). A more facile procedure was subsequently developed for the synthesis of 1-substituted 2-amino-3- cyanopyrroles. N-Substituted aminoacetaldehyde dimethyl acetals (7a-c) were condensed with malononitrile in the presence of p-toluenesulfonic acid monohydrate to afford the corresponding 1-substituted 2-amino-3-cyanopyrroles (1a-c).",
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N2 - (Equation Presented) 1-Benzyl-3-cyanopyrrole-2-carbonyl azide (5) underwent a Curtius rearrangement followed by quenching with alcohols to form the corresponding carbamates (6a-c). The carbamates 6a,b were unblocked to give the desired 2-amino-1-benzyl-3-cyanopyrrole (1a). A more facile procedure was subsequently developed for the synthesis of 1-substituted 2-amino-3- cyanopyrroles. N-Substituted aminoacetaldehyde dimethyl acetals (7a-c) were condensed with malononitrile in the presence of p-toluenesulfonic acid monohydrate to afford the corresponding 1-substituted 2-amino-3-cyanopyrroles (1a-c).

AB - (Equation Presented) 1-Benzyl-3-cyanopyrrole-2-carbonyl azide (5) underwent a Curtius rearrangement followed by quenching with alcohols to form the corresponding carbamates (6a-c). The carbamates 6a,b were unblocked to give the desired 2-amino-1-benzyl-3-cyanopyrrole (1a). A more facile procedure was subsequently developed for the synthesis of 1-substituted 2-amino-3- cyanopyrroles. N-Substituted aminoacetaldehyde dimethyl acetals (7a-c) were condensed with malononitrile in the presence of p-toluenesulfonic acid monohydrate to afford the corresponding 1-substituted 2-amino-3-cyanopyrroles (1a-c).

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