Bibliographic Details
| Title: |
Evaluation of Phenyldiazenyl as a Protective/Activating Group in Lithiation–Substitution Reactions of Tetrahydroisoquinolines. |
| Authors: |
Kaur, Babaldeep, Kaur, Manjot, Singh, Pushpinder, Sharma, Esha, Batra, Aanchal, Kaur, Amarjit, Singh, Kamal Nain |
| Source: |
Synlett; Aug2024, Vol. 35 Issue 13, p1577-1583, 7p |
| Subject Terms: |
HALOALKANES, TETRAHYDROISOQUINOLINES, CARBANIONS, ELECTROPHILES, ISOCYANATES |
| Abstract: |
Phenyldiazenyl moiety has been utilized both as a protective and activating group to synthesize C-1-substituted tetrahydroisoquinolines via lithiation–substitution strategy. This reaction sequence involves generation of α-amino carbanions, derived from N -phenyldiazenyl tetrahydroisoquinolines, followed by coupling with various electrophiles, e.g., aldehyde, ketones, alkyl halide, oxiranes, isocyanates, and with in situ generated arynes. Deprotection of the protecting group was carried out under acidic conditions to afford the desired α-substituted products in moderate to good yields. So, triazene as a protecting/directing group and its compatibility with strong bases provide a good synthetic utility for the synthesis of a variety of α-substituted secondary amines via lithiation substitution reaction. [ABSTRACT FROM AUTHOR] |
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| Database: |
Complementary Index |
