Carboline-1 -carboxamide

Phenol-type resins 13-15 have also been used to prepare LH-RH, enkephalin and bradykinin peptide analogs. Peptides were successfully cleaved by ammonoly-sis (NH3 in MeOH-DMF or DMF, 5-18h) or aminolysis with protected amino acid or peptide esters bearing the free a-amino group [24, 25, 35]. Marshall s mercaptophenol resin (16) has been used to prepare libraries of piperazine-2-carboxamides (consisting of 22 different amines) and 6-carboxybenzopyran-4-ones. Cleavage was performed using an excess of appropriate amines in pyridine for 24 to 48 h [36, 37]. Tetrahydro-P-carboline-3-carboxamides have also been similarly synthesized and released [38]. 

Manabe, S., Y. Juan, O. Wada, A. Ueki, and Y. Kanai A-Methyl-P-carboline-3-carboxamide (FG 7142) An anxiogenic agent in cigarette smoke condensate and its mechanism of formation Environ. Pollut. 89 (1995) 329-335. 

Fig. 19.1 Structure of some P-carbolines synthesized biologically and chemically (1) Prom plant (a, b, c, d, e, f, and g) (2) Prom animals (a, d, g,h, i, j, and k) (3) Synthesized chanically (1 and m). (a) Harman (b) harmaline (c) harmine (d) norharman (e) hatmol (f) harmalol (g) tetrahydrohatmine (h) tryptoline (i) pinoline (j) l-(2-guanidinoethyl)-l,2,3,4-tetrahydro-6-hydroxymethyl)-P-carboline [37] (k) manzamine A [39] (1) 3-ethyl-l-phenyM,9-dihydro-3//-beta-carbolme (m) lV-butyl-1-(4-dimethylammo)phenyl-l,2,3,4-tetrahydro-P-carboline-3-carboxamide [40]...

The Padwa group has reported the synthesis of substituted -carbolines III-IO via gold(III)-catalyzed cycloisomerization of A -propargylindole-2-carboxamides III-9 (R = H) (Scheme 4.9) [44, 45]. Alkyne-substituted Af-propargylindole-2-carboxamides III-9 (R — Ar) also cyclized to form azepino[3,4-h]insol-l-ones III-ll using AuCl, AuCls, and PtClj [46]. 

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